Reaktion #1195963

Reaktionsgleichung

7-Amino-1H-1,3-azaphospholo[4,5-d]pyrimidine

sodium hydride

1-bromohexane

MeOH

compound 10

7-Amino-1H-1,3-azaphospholo[4,5-d]pyrimidine

→

7-Amino-1-(n-hexyl)-1,3-azaphospholo[4,5-d]pyrimidine

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added under an argon atmosphere
2. 2
   workup.WAITThe reaction was continued for 3 h
3. 3
   Sonstigethe solvent was evaporated
4. 4
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (150 mL)
5. 5
   Waschenwashed with water (25 mL)
6. 6
   SonstigeOrganic layer was separated
7. 7
   Extraktionthe aqueous layer was extracted with dichloromethane (2×50 mL)
8. 8
   TrocknenThe combined organic layer was dried (Na2SO4)
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was purified by silica gel column (2×15 cm) chromatography
11. 11
    Wascheneluting with dichloromethane containing 0-4% methanol
12. 12
    workup.ADDITIONThe appropriate fractions containing the desired product
13. 13
    Sonstigewere evaporated
14. 14
    Sonstigeto yield 0.53 g (68%), mp 220-222° C

Vorschrift

7-Amino-1H-1,3-azaphospholo[4,5-d]pyrimidine (compound 10, 0.5 g, 3.29 mmol) was suspended in dry DMF to which sodium hydride (160 mg, 4 mmol, 60% dispersion in mineral oil) was added under an argon atmosphere. The mixture was stirred at room temperature for 40 min and 1-bromohexane (0.56 mL, 4 mmol) was added. The reaction was continued for 3 h and the solvent was evaporated. The residue was dissolved in dichloromethane (150 mL) and washed with water (25 mL). Organic layer was separated and the aqueous layer was extracted with dichloromethane (2×50 mL). The combined organic layer was dried (Na2SO4) and evaporated. The residue was purified by silica gel column (2×15 cm) chromatography eluting with dichloromethane containing 0-4% methanol. The appropriate fractions containing the desired product were evaporated to yield 0.53 g (68%), mp 220-222° C. Ir (KBr): ν690 (=P-C), 1220 (-P=CH), and 3295 (NH2) cm-1. Uv (pH 1): λmax 254 nm (ε23,700), 282 (11,500), and 314 (5200); (MeOH): λmax 266 (ε31,600); (pH 11): λmax 266 nm (ε33,300), and 330 (2200). 31 p nmr (DMSO-d6): 63.21. 1H nmr (DMSO-d6): δ 0.80(t, 3 H, CH3), 1.23 (br s, 6 H, 3CH2), 1.92 (t, 2 H, CH2), 4.24 (t, 2 H, NCH2), 8.15 and 8.23 (2s, 2 H, NH2), 8.44 (d, 1 H, C5H), and 8.86 (d, 1 H, J=58.5 Hz, C2H). Anal. Calcd. for C11H17N4P: C, 55.92; H, 7.25; N, 23.72. Found: C, 55.49; H, 7.31; N, 23.28.

Quelle