Methyl Acrylate → Ethyl 5-benzyloxy-1-(2-methoxycarbonylethyl)-2-methylthio-6-oxo-1,6-dihydro-pyrimidine-4-carboxylate

HRID 458680Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[NH:13][C:12]([S:16][CH3:17])=[N:11][C:10]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].[F-].[Cs+]>>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH2:25][CH2:24][C:23]([O:27][CH3:28])=[O:26])[C:12]([S:16][CH3:17])=[N:11][C:10]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 7294Methyl Acrylate

HCID 25953Cesium fluoride

HCID 135772690Ethyl 5-(benzyloxy)-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 18442530Ethyl 5-benzyloxy-1-(2-methoxycarbonylethyl)-2-methylthio-6-oxo-1,6-dihydro-pyrimidine-4-carboxylateYield 82%

Procedure

Reaction of intermediate 1, ethyl 5-benzyloxy-2-methylthio-6-oxo-1,6-dihydro-pyrimidine-4-carboxylate, (1.500 g, 4.68 mmol) with methyl acrylate (25 ml) and cesium fluoride (0.19 g) for 18 h as described for the preparation of intermediate 6 gave 1.560 g (82% yield) of the title ester as a white solid; mp 62–63° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.31 (3H, t, J=7.1 Hz, CH3), 2.59 (3H, s, SCH3), 2.78 (2H, m, CH2), 3.72 (3H, s, OCH3), 4.34 (4H, m, OCH2 and NCH2), 5.19 (2H, s, OCH2), 7.34 (3H, m, aromatics), 7.46 (2H, m, aromatics). MS (ESI+) m/z 407 [M+H+].

Sources & evidence

ORD record: ord-264f755969854e82b476a607254c9c5e
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192948B2

Reaction notes

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