(2R,3S)-2-methylmorpholine-3-carboxylic acid → (2R,3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(methoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-2-methylmorpholine-3-carboxylic acid

HRID 524604Notes

Reaction equation

HRID 524604 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][CH3:18])=[O:16])=[C:13]([CH2:19]Br)[NH:12][C:11]([C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[N:10]1.[CH3:26][C@H:27]1[O:32][CH2:31][CH2:30][NH:29][C@@H:28]1[C:33]([OH:35])=[O:34]>>[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:21]2[S:22][CH:23]=[CH:24][N:25]=2)[NH:12][C:13]([CH2:19][N:29]2[CH2:30][CH2:31][O:32][C@H:27]([CH3:26])[C@H:28]2[C:33]([OH:35])=[O:34])=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 45791333(2R,3S)-2-methylmorpholine-3-carboxylic acidHCID 118107576Methyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 73295801(2R,3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(methoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)-2-methylmorpholine-3-carboxylic acidYield 49.5%

Procedure

Methyl 4-(2-bromo-4-fluorophenyl)-6-(bromomethyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate (0.93 g, 1.9 mmol) was reacted with (2R,3S)-2-methyl morpholine-3-carboxylic acid (0.28 g, 1.9 mmol) according to the procedure as described in Example 34 to give the title compound as a yellow solid (0.52 g, 49%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-17b514882bb345138db1204950a0a0ab
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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