Triethylamine → 3-methyl-2-((2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholino)-6-(pyrimidin-4-yl)pyrimidin-4(3H)-one

HRID 2063350Notes

Reaction equation

HRID 2063350 reaction equation
Cl[C:2]1[N:3]([CH3:15])[C:4](=[O:14])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[N:7]=1.Cl.[CH3:17][C:18]1[N:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([C@@H:29]3[O:34][CH2:33][CH2:32][NH:31][CH2:30]3)=[CH:25][CH:24]=2)[O:20][N:19]=1.C(N(CC)CC)C>>[CH3:15][N:3]1[C:4](=[O:14])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[N:7]=[C:2]1[N:31]1[CH2:32][CH2:33][O:34][C@@H:29]([C:26]2[CH:27]=[CH:28][C:23]([C:21]3[O:20][N:19]=[C:18]([CH3:17])[N:22]=3)=[CH:24][CH:25]=2)[CH2:30]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one2×HCID 66842520(2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine hydrochloride2×

Product 1

HCID 251954623-methyl-2-((2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholino)-6-(pyrimidin-4-yl)pyrimidin-4(3H)-one

Procedure

To a solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (intermediate 1, 12.6 g, 56.6 mmol) and (2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholine hydrochloride (intermediate 19, 16.7 g, 59.3 mmol) was added triethylamine (17.2 g, 170 mmol) at room temperature and the mixture was stirred at room temperature for 8 hours. The organic solvent was removed under reduced pressure, and the resulting crude product was washed with ethyl acetate and water and dried under reduced pressure to afford 3-methyl-2-((2S)-2-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)morpholino)-6-(pyrimidin-4-yl)pyrimidin-4(3H)-one (compound of the present invention, 23.7 g, 97%).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. washthe resulting crude product was washed with ethyl acetate and water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1c267c16cfda44afa439a9ac151d61ef
Source dataset
uspto-grants-2012_10
Patent number
US08288383B2

Reaction notes

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