Cyano-borohydride → HCID 57497093, compound

HRID 2409188Notes

Reaction equation

HRID 2409188 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.[CH3:21][C:22]1[N:23]=[C:24]([C:28](=O)[CH3:29])[S:25][C:26]=1[CH3:27].C([BH3-])#N>[Zn]>[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:28]([C:24]3[S:25][C:26]([CH3:27])=[C:22]([CH3:21])[N:23]=3)[CH3:29])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 498716Cyano-borohydrideHCID 27562722-Acetyl-4,5-dimethylthiazoleHCID 57497157(S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one2×

Product 1

HCID 57497093HCID 57497093, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

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-(4,5-dimethyl-thiazol-2-yl)-ethanone with zinc-modified cyanoborohydride yielded a mixture of epimers of the title compound as a colorless solid. MS (ESI): m/z=418.4 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-b7c13a63537c4a7c85d5a9cc8fad1b64
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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