Pyrimidine-2-carbaldehyde → (S)-2-Amino-6-{2-fluoro-5-[(pyrimidin-2-ylmethyl)-amino]-phenyl}-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one

HRID 2409171Notes

Reaction equation

HRID 2409171 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.[N:21]1[CH:26]=[CH:25][CH:24]=[N:23][C:22]=1[CH:27]=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][CH2:27][C:22]3[N:23]=[CH:24][CH:25]=[CH:26][N:21]=3)[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 13751953Pyrimidine-2-carbaldehydeHCID 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 57497088(S)-2-Amino-6-{2-fluoro-5-[(pyrimidin-2-ylmethyl)-amino]-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 pyrimidin-2-carbaldehyde using decaborane yielded the title compound as a white foam. MS (ESI): m/z=371.3 [M+H]+.

Sources & evidence

ORD record
ord-00c28f6bf30747099e91708999f8d18f
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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