HCID 78322881, compound → HCID 86711307, compound

HRID 336174Notes

Reaction equation

Br[C:2]1[N:11]([CH2:12][C@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:14]=[CH2:15])[C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2.NC1C2C(C3C=NC4C(C=3)=CC=CC=4)=C3N(C=2N=CN=1)C[C@@H](NC(=O)OC(C)(C)C)CC3>>[Si:17]([O:16][C@@H:13]1[CH2:14][CH2:15][C:2]2[N:11]([C:5]3[N:6]=[CH:7][N:8]=[C:9]([NH2:10])[C:4]=3[C:3]=2[C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:12]1)([C:20]([CH3:23])([CH3:21])[CH3:22])([CH3:18])[CH3:19]

Participants

Reactant 2

HCID 78322881HCID 78322881, compound

HCID 86711308HCID 86711308, compound

Product 1

HCID 86711307HCID 86711307, compoundYield 64.3%

Procedure

In accordance with Example 10, except that the (R)-6-bromo-7-(2-((tert-butyldimethylsilyl)oxy)but-3-en-1-yl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (1.0 g) obtained in Reference Example 11 was used in place of the (S)-tert-butyl (1-(4-amino-6-bromo-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate obtained in Example 10, (R)-8-((tert-butyldimethylsilyl)oxy)-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine (546 mg) (yield: 64%) was obtained.

Sources & evidence

ORD record: ord-716a6bd1b0e4413db272b1686ade7a7c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889666B2

Reaction notes

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