Methyl trifluoromethyl ketone → (S)-2-Amino-6-[2-fluoro-5-(2,2,2-trifluoro-1-methyl-ethylamino)-phenyl]-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

HRID 2409156Notes

Reaction equation

HRID 2409156 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:11])([CH3:10])[C@:4]([C:13]2[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1.[F:21][C:22]([F:27])([F:26])[C:23](=O)[CH3:24].[B][B][B][B][B][B][B][B][B][B]>>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([CH3:10])([CH3:11])[C@:4]([C:13]2[CH:18]=[C:17]([NH:19][CH:23]([CH3:24])[C:22]([F:27])([F:26])[F:21])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 9871Methyl trifluoromethyl ketoneHCID 57497157(S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one2×HCID 178419135HCID 178419135, compound

Product 1

HCID 57497051(S)-2-Amino-6-[2-fluoro-5-(2,2,2-trifluoro-1-methyl-ethylamino)-phenyl]-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

Procedure

The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and 1,1,1-trifluoro-propan-2-one using decaborane yielded a mixture of epimers of the title compound as a white foam. MS (ESI): m/z=375.3 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-36d7b5a7e40c4897b68d4a7311e7ec36
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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