Aniline → 2-anilino-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4(3H)-one

HRID 68335Notes

Reaction equation

HRID 68335 reaction equation
C[O:2][C:3]1[N:8]=[C:7](S(C)(=O)=O)[N:6]=[C:5]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[N:15](S(C3C=CC=CC=3)(=O)=O)[CH:14]=2)[CH:4]=1.[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN1CCCC1=O>[NH:31]([C:7]1[NH:8][C:3](=[O:2])[CH:4]=[C:5]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[N:6]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 668887123-(6-methoxy-2-(methylsulfonyl)pyrimidin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 1359628082-anilino-6-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of EXAMPLE 1B (0.089 g, 0.20 mmol), and aniline (0.2 mL) in N-methylpyrrolidone (3 mL) was heated in a microwave at 235° C. for 1.5 hours. The mixture was concentrated and purified by reverse phase HPLC to provide the title compound. MS (ESI) m/e 304 (M+H)+; 1H NMR (DMSO-d6) δ 6.33 (s, 1H), 7.06-7.18 (m, 2H), 7.34-7.45 (m, 2H), 7.68 (d, J=7.67 Hz, 2H), 8.23 (s, 1H), 8.26-8.31 (m, 1H), 8.56 (d, J=7.67 Hz, 1H), 8.84 (s, 1H), 12.22 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-c80c3e2947514853bd6a11827221ae53
Source dataset
uspto-grants-2014_09
Patent number
US08822446B2

Reaction notes

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