Reaction #166346

Reaction equation

compound 269

tert-Butyl 4-(6-((9-cyclopentyl-7-methoxy-9H-pyrido[3′,2′:4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

hydrochloric acid

→

compound 270

Yield 108.2%

9-Cyclopentyl-2-((5-(1-piperazinyl)-2-pyridinyl)amino)-9H-pyrido[3′,2′:4,5]-pyrrolo[2,3-d]pyrimidin-7-ol

Yield 108.2%

Conditions

Workup

1. 1
   OtherA 10 mL reaction tube vessel
2. 2
   Otheran additional 30 minutes
3. 3
   Otherat 140° C
4. 4
   FiltrationThe resulting solution was filtered through a 0.45 μM
5. 5
   Filtrationfilter
6. 6
   Washwashed with water
7. 7
   OtherThe solvent was removed in vacuo

Procedure

A 10 mL reaction tube vessel was charged with compound 269 (56.0 mg, 103 μmol) and concentrated hydrochloric acid (2.00 mL, 103 μmol). The reaction was heated with microwave energy (300 W) at 120° C. for 1 hour, then an additional 30 minutes at 140° C. The resulting solution was filtered through a 0.45 μM filter and washed with water. The solvent was removed in vacuo, and the residue coevaporated with water (10 mL) and then methanol (2×, 10 mL) to give compound 270 as a yellow solid (48 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.63-11.91 (m, 2 H) 9.40 (br. s., 4 H) 9.19 (s, 1 H) 8.50 (d, J=8.61 Hz, 1 H) 8.04 (d, J=2.74 Hz, 1 H) 7.99 (dd, J=9.39, 2.74 Hz, 1 H) 7.51 (d, J=9.39 Hz, 1 H) 6.69-6.78 (m, 1 H) 5.35 (quin, J=8.71 Hz, 1 H) 3.37-3.51 (m, 4 H) 3.20-3.34 (m, 4 H) 2.06-2.18 (m, 2 H) 1.93-2.06 (m, 2 H) 1.66-1.82 (m, 2 H) ppm.

Source