Ethyl 2-bromo-1,3-thiazole-4-carboxylate → Ethyl 2-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate

HRID 624613Notes

Reaction equation

[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:10]([C:11]3C=C(C=CC=3)C#N)=[C:6]2[C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29].CN1C2=CN(COCC[Si](C)(C)C)C(B(O)O)=C2C(=O)N(C)C1=O.BrC1[S:56][CH:57]=[C:58]([C:60]([O:62][CH2:63][CH3:64])=[O:61])[N:59]=1>>[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[C:10]([C:11]3[S:56][CH:57]=[C:58]([C:60]([O:62][CH2:63][CH3:64])=[O:61])[N:59]=3)=[C:6]2[C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29]

Participants

Reactant 3

HCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylate

HCID 867229261,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid

HCID 867229273-(1,3-Dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Product 1

HCID 86722932Ethyl 2-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thiazole-4-carboxylate

Procedure

The title compound was prepared analogously to 3-(1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (Intermediate Ga, step 3) from 1,3-dimethyl-2,4-dioxo-6-((2-(trimethylsilyl)ethoxy)methyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-ylboronic acid (Intermediate Ga Step 2) and commercially available ethyl 2-bromothiazole-4-carboxylate.

Sources & evidence

ORD record: ord-5716e6b2b6be4bba959c0b7ca82d2305
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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