HCID 59244797, compound → HCID 59244311, compound

HRID 912275Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:51])[C:9]([N:11]2[C:15]3[N:16]=[C:17]([N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)[N:18]=[C:19]([C:20]4[CH:21]=[N:22][C:23]([N:26](CC5C=CC(OC)=CC=5)CC5C=CC(OC)=CC=5)=[N:24][CH:25]=4)[C:14]=3[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.OCCN1CCN(C2C=CC(N(C)C(N3C4N=C(N5CCOCC5)N=C(C5C=NC(N(CC6C=CC(OC)=CC=6)CC6C=CC(OC)=CC=6)=NC=5)C=4CC3)=O)=CC=2)CC1>>[CH3:51][N:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:9]([N:11]1[C:15]2[N:16]=[C:17]([N:45]3[CH2:50][CH2:49][O:48][CH2:47][CH2:46]3)[N:18]=[C:19]([C:20]3[CH:25]=[N:24][C:23]([NH2:26])=[N:22][CH:21]=3)[C:14]=2[CH2:13][CH2:12]1)=[O:10]

Participants

Reactant 2

HCID 59244797HCID 59244797, compound

HCID 67385453HCID 67385453, compound

Product 1

HCID 59244311HCID 59244311, compoundYield 22.1%

Procedure

Using 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 (4-bromo-phenyl)-methyl-amide (121 mg) obtained in Step B in Example 1-D-160 instead 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 (3-bromo-phenyl)-methyl-amide, in the same manner as Step C in Example 1-D-153, 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{4-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-phenyl}-methyl-amide was obtained. The PMB groups were removed according to Deprotection method 3, to obtain the desired compound (D-162) as a colorless solid (17.1 mg, 38%)) and the desired compound (D-163) as a colorless solid (15.4 mg, 11%).

Workup

customThe PMB groups were removed

Sources & evidence

ORD record: ord-a1865c7a41e74384a0aaf66599a6486f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022205B2

Reaction notes

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