Ethyl isothiocyanatoformate → 1-[2-{[tert-Butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-one

HRID 1171774Notes

Reaction equation

C([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][C:10]=1[NH:11][CH2:12][CH:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=O)C.C(OC([N:35]=[C:36]=[S:37])=O)C>>[Si:23]([O:22][CH:13]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)[CH2:12][N:11]1[C:10]2[CH:9]=[CH:8][NH:7][C:6]=2[C:4](=[O:3])[NH:35][C:36]1=[S:37])([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24]

Participants

Reactant 2

HCID 85320Ethyl isothiocyanatoformate

HCID 670684993-{[2-{[tert-Butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)ethyl]amino}-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 866231281-[2-{[tert-Butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)ethyl]-2-thioxo-1,2,3,5-tetrahydro-pyrrolo[3,2-d]pyrimidin-4-oneYield 90%

Procedure

The title compound (0.07 g, 90%) was prepared in accordance with general method B using 3-{[2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-methoxyphenyl)ethyl]amino}-1H-pyrrole-2-carboxylic acid ethyl ester (0.13 g, 0.31 mmol) and ethoxycarbonyl isothiocyanate (0.042 mL, 0.37 mmol).

Sources & evidence

ORD record: ord-d75ea047d2a1473389ccc969368a3445
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829707B2

Reaction notes

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