(S)-Methyl 6,6-dimethyl-morpholine-3-carboxylate → (3S)-methyl 4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-6,6-dimethylmorpholine-3-carboxylate

HRID 524822Notes

Reaction equation

HRID 524822 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH2:20]Br)[NH:12][C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)=[N:10]1.[CH3:27][C:28]1([CH3:38])[CH2:33][NH:32][C@H:31]([C:34]([O:36][CH3:37])=[O:35])[CH2:30][O:29]1>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:10]=[C:11]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[NH:12][C:13]([CH2:20][N:32]2[CH2:33][C:28]([CH3:27])([CH3:38])[O:29][CH2:30][C@H:31]2[C:34]([O:36][CH3:37])=[O:35])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

3

Reactant 2

HCID 53338736(S)-Methyl 6,6-dimethyl-morpholine-3-carboxylateHCID 59495567Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 118107615(3S)-methyl 4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-6,6-dimethylmorpholine-3-carboxylateYield 27%

Procedure

Ethyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.76 g, 1.52 mmol) was reacted with (S)-methyl 6,6-dimethylmorpholine-3-carboxylate (0.26 g, 1.52 mmol) according to the procedure as described in Example 24 to give the title compound as yellow oil (0.24 g, 27%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-439e9174148342a59bd2aaad5a4311ee
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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