반응 #2469289

반응 방정식

3-methyl-pyrrolo[3,2-c]pyridin-1-ylamine

2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid

HATU

DIPEA

NaHCO3

→

2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide

수율 36.0%

용매

DMF

water

반응 조건

후처리

1. 1
   온도is heated at 1500 C
2. 2
   workup.ADDITIONis added
3. 3
   추출the mixture is extracted with EtOAc
4. 4
   기타The organic layer is separated
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타The residue is first purified by silica gel column chromatography
9. 9
   세척eluting with 10% MeOH in DCM
10. 10
    기타recrystallized from EtOAc

실험 절차

A mixture of 3-methyl-pyrrolo[3,2-c]pyridin-1-ylamine (224 mg, 1.52 mmol), 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (354 mg, 1.52 mmol), HATU (693 mg, 1.82 mmol) and DIPEA (593 mg, 4.59 mmol) in DMF (8 mL) is heated at 1500 C. for 1 h. The reaction is quenched with water, NaHCO3 (168 mg, 2 mmol) is added and the mixture is extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated. The residue is first purified by silica gel column chromatography eluting with 10% MeOH in DCM and then recrystallized from EtOAc to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (3-methyl-pyrrolo[3,2-c]pyridin-1-yl)-amide (198 mg). MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.12 (s, 1H), 8.86 (s, 1H), 8.35 (d, 1H), 8.15-8.31 (m, 2H), 7.47-7.60 (m, 2H), 7.35 (s, 1H), 7.29 (t, 1H), 2.84 (s, 3H), 2.44 (s, 3H).

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