Thiophosgene → 4-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbothioic acid [4-(4-methyl-piperazine-1-carbonyl)-phenyl]-amide

HRID 912322Notes

Reaction equation

HRID 912322 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[CH:13][C:12]([C:15]3[C:16]4[CH2:29][CH2:28][NH:27][C:17]=4[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=3)=[CH:11][N:10]=2)=CC=1.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([N:50]2[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]2)=[O:49])=[CH:44][CH:43]=1.[C:57](Cl)(Cl)=[S:58]>>[CH3:56][N:53]1[CH2:52][CH2:51][N:50]([C:48]([C:45]2[CH:44]=[CH:43][C:42]([NH:41][C:57]([N:27]3[C:17]4[N:18]=[C:19]([N:21]5[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[N:20]=[C:15]([C:12]5[CH:11]=[N:10][C:9]([NH2:8])=[N:14][CH:13]=5)[C:16]=4[CH2:29][CH2:28]3)=[S:58])=[CH:47][CH:46]=2)=[O:49])[CH2:55][CH2:54]1

Participants

4

Reactant 3

HCID 10040ThiophosgeneHCID 231408(4-Aminophenyl)(4-methylpiperazin-1-yl)methanoneHCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

Product 1

HCID 592445394-(2-Amino-pyrimidin-5-yl)-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbothioic acid [4-(4-methyl-piperazine-1-carbonyl)-phenyl]-amideYield 33%

Procedure

Using bis-(4-methoxy-benzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine (80.9 mg) and (4-amino-phenyl)-(4-methyl-piperazin-1-yl)-methanone (39.5 mg) obtained in Step B instead of 4-(4-ethyl-piperazin-1-yl)-2,6-difluoro-phenylamine, and thiophosgene (22.9 μl) instead of triphosgene, in the same manner as Step D in Example 1-D-18, 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carbothioic acid [4-(4-methyl-piperazine-1-carbonyl)-phenyl]-amide was obtained as a crude product. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-231) as a yellow solid (28.1 mg, 33%).

Workup

  1. customThe PMB groups were removed

Sources & evidence

ORD record
ord-57ecf27d40a84009a13b222741b9917a
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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