Trifluoroacetaldehyde → (S)-2-Amino-6-(2-fluoro-5-(2,2,2-trifluoroethylamino)phenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409162Notes

Reaction equation

HRID 2409162 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:26])([F:25])[CH:23]=O.[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][CH2:23][C:22]([F:26])([F:25])[F:21])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 65564TrifluoroacetaldehydeHCID 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 57497012(S)-2-Amino-6-(2-fluoro-5-(2,2,2-trifluoroethylamino)phenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-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 trifluoro-acetaldehyde using decaborane yielded the title compound as a colorless waxy solid. MS (ESI): m/z=361.3 [M+H]+.

Sources & evidence

ORD record
ord-02f79576d5bb44e2a543be3da78e8ca4
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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