Ammonium Hydroxide → 5-iodo-7-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 243313Notes

Reaction equation

HRID 243313 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:16]4[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]=3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:28].[OH-]>CO>[I:11][C:10]1[C:3]2[C:2]([NH2:28])=[N:7][CH:6]=[N:5][C:4]=2[N:8]([CH2:12][C:13]2[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[N:14]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 866688814-chloro-5-iodo-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 601616285-iodo-7-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-chloro-5-iodo-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (1.0 g, 2 mmol) in NH4OH (5 mL) and MeOH (10 mL) was stirred at 90° C. in a sealed tube overnight. Then the mixture was filtered. The precipitate was purified by P-TLC to give 140 (0.4 g, yield 42%) as a white solid. LCMS (ESI), M+H+=465.04 1HNMR (400 MHz, DMSO) δ 5.518 (s, 2H), 6.574 (s, 2H), 7.128 (s, 2H), 7.210-7.232 (m, 2H), 7.343 (s, 1H), 7.521-7.622 (m, 6H), 7.968 (s, 1H)

Workup

  1. filtrationThen the mixture was filtered
  2. customThe precipitate was purified by P-TLC

Sources & evidence

ORD record
ord-374323efc9a64008a17917653f1fcb7c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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