2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 6-[2-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentylamino]-4-methyl-2,3-benzoxazin-1-one

HRID 430473Notes

Reaction equation

HRID 430473 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]2[C:30](=[O:31])[O:29][N:28]=[C:27]([CH3:32])[C:26]=2[CH:33]=1.CN1CCCN(C)C1=O>O1CCCC1>[OH:11][C:10]([C:13]([F:16])([F:15])[F:14])([CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:19][CH3:20])([CH3:18])[CH3:17])[CH2:12][NH:21][C:22]1[CH:23]=[CH:24][C:25]2[C:30](=[O:31])[O:29][N:28]=[C:27]([CH3:32])[C:26]=2[CH:33]=1

Participants

5

Reactant 3

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 111829366-amino-4-methyl-2,3-benzoxazin-1-oneHCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Product 1

HCID 154635516-[2-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentylamino]-4-methyl-2,3-benzoxazin-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

584 mg of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methyl-propyl]-2-trifluoromethyl-oxiran, 282 mg of 6-amino-4-methyl-2,3-benzoxazin-1-one and 1 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2[1H]-pyrimidinone are heated to 120° C. for 6 hours. After 1 ml of tetrahydrofuran is added, it is chromatographed on silica gel, and the title compound is eluted with hexane/ethyl acetate/tetrahydrofuran (55:40:5), flash point 178-179° C.

Workup

  1. customit is chromatographed on silica gel
  2. washthe title compound is eluted with hexane/ethyl acetate/tetrahydrofuran (55:40:5), flash point 178-179° C.

Sources & evidence

ORD record
ord-e2ffd892c314470c93c2f2555b3d26d4
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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