Ammonium Hydroxide → 7-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 243310Notes

Reaction equation

HRID 243310 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:11][C:12]3[N:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15]4[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:27].[OH-]>CO>[C:17]1([N:16]2[C:15]3[CH:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]=[C:12]2[CH2:11][N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:27])[C:3]=3[CH:10]=[CH:9]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 866688804-chloro-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 681577057-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]-pyrimidine (1.0 g, 2.7 mmol) in NH4OH (5 mL) and MeOH (10 mL) was stirred at 90° C. in a sealed tube overnight. Then the mixture was concentrated in vacuo. The residue was purified by P-TLC to give 139 (0.2 g, yield 22%) as a white solid. LCMS (ESI), M+H+=339.14. 1HNMR (400 MHz, CDCl3) δ 5.505 (s, 1H), 6.503 (s, 1H), 6.936 (s, 2H), 7.031 (s, 1H), 7.205-7.209 (q, J=1.6 Hz, 1H), 7.219-7.228 (m, 2H), 7.490-7.540 (m, 5H), 7.555-7.559 (d, J=1.6 Hz, 1H), 7.910 (s, 1H)

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. customThe residue was purified by P-TLC

Sources & evidence

ORD record
ord-ec8811aba63244ccbccab46794bf693c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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