Urea → HCID 67385222, compound

HRID 912356Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:40]=[CH:39][C:6]([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=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)=[CH:5][CH:4]=1.[N:41]([C:44]1[C:45]([CH3:50])=[N:46][CH:47]=[CH:48][CH:49]=1)=[C:42]=[O:43].NC(N)=O>>[CH3:50][C:45]1[C:44]([NH:41][C:42]([N:27]2[C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[N:20]=[C:15]([C:12]4[CH:11]=[N:10][C:9]([N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:40][CH:39]=5)[CH2:30][C:31]5[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=5)=[N:14][CH:13]=4)[C:16]=3[CH2:29][CH2:28]2)=[O:43])=[CH:49][CH:48]=[CH:47][N:46]=1

Participants

Reactant 3

HCID 1176Urea

HCID 45258862Bis-(4-methoxybenzyl)-[5-(2-morpholin-4-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)-pyrimidin-2-yl]-amine

HCID 569726683-Isocyanato-2-methylpyridine

Product 1

HCID 67385222HCID 67385222, compound

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 (80.0 mg, 0.148 mmol) and a crude product (59.7 mg) of 3-isocyanato-2-methyl-pyridine obtained in Step A instead of 2-chlorophenyl isocyanate, urea was formed in the same manner as Example 1-D-217, to obtain a crude product of 4-{2-[bis-(4-methoxy-benzyl)-amino]-pyrimidin-5-yl}-2-morpholin-4-yl-5,6-dihydro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid (2-methyl-pyridin-3-yl)-amide as a yellow solid (103 mg), and then the PMB groups were removed according to the above Deprotection method 3, to obtain the desired compound (D-274) as a yellow powder (14.4 mg, 22%).

Sources & evidence

ORD record: ord-cd1f746fdbec465db9e87dddac610bc7
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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