Bromomethylcyclopropane → ethyl 2-(3-(cyclopropylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylate

HRID 560706Notes

Reaction equation

FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.[CH3:18][C:19]1[N:20]=[C:21]([N:29]2[CH2:34][CH2:33][CH2:32][NH:31][C:30]2=[O:35])[S:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[CH:17]1([CH2:16][N:31]2[CH2:32][CH2:33][CH2:34][N:29]([C:21]3[S:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:19]([CH3:18])[N:20]=3)[C:30]2=[O:35])[CH2:15][CH2:14]1

Participants

Reactant 3

HCID 81503Bromomethylcyclopropane

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

HCID 58031510ethyl 4-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)thiazole-5-carboxylate

Product 1

HCID 58031414ethyl 2-(3-(cyclopropylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylate

Procedure

Following the procedure as described in Example 13, making variations as required to replace 4-(trifluoromethyl)benzyl bromide with (bromomethyl)cyclopropane to react with ethyl 4-methyl-2-(2-oxotetrahydropyrimidin-1(2H)-yl)thiazole-5-carboxylate, the title compound was obtained as a colorless solid in quantitative yield: MS (ES+) m/z 324.2 (M+1).

Sources & evidence

ORD record: ord-66c42d3a6cf54e92ab94c27cdbb4e876
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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