2-Bromo-4-chloro-1,3-thiazole → 3-(6-(3-((tert-Butyldimethylsilyl)oxy)-2-(2-(4-chlorothiazol-2-yl)-2-oxoethoxy)propyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

HRID 624576Notes

Reaction equation

HRID 624576 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:33][CH2:34][C:35](N(OC)C)=[O:36])[CH2:11][N:12]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=2)=[C:19]2[C:14]([N:15]([CH3:32])[C:16](=[O:31])[N:17]([CH3:30])[C:18]2=[O:29])=[CH:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:42]1[S:43][CH:44]=[C:45]([Cl:47])[N:46]=1>>[Si:1]([O:8][CH2:9][CH:10]([O:33][CH2:34][C:35]([C:42]1[S:43][CH:44]=[C:45]([Cl:47])[N:46]=1)=[O:36])[CH2:11][N:12]1[C:20]([C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=2)[C:27]#[N:28])=[C:19]2[C:14]([N:15]([CH3:32])[C:16](=[O:31])[N:17]([CH3:30])[C:18]2=[O:29])=[CH:13]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 151419642-Bromo-4-chloro-1,3-thiazoleHCID 867229002-((1-((tert-Butyldimethylsilyl)oxy)-3-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl)oxy)-N-methoxy-N-methylacetamide

Product 1

HCID 867229023-(6-(3-((tert-Butyldimethylsilyl)oxy)-2-(2-(4-chlorothiazol-2-yl)-2-oxoethoxy)propyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Procedure

The title compound was prepared from 2-((1-((tert-butyldimethylsilyl)oxy)-3-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl)oxy)-N-methoxy-N-methylacetamide and 2-bromo-4-chlorothiazole analogously to Example 13, step 3;

Sources & evidence

ORD record
ord-ec753dc587ac4f639a9aed6737f7cf90
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

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