HCID 10397833, compound → HCID 57516116, compound

HRID 2409175Notes

Reaction equation

HRID 2409175 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.[CH2:21]([O:23][C:24](=[O:34])[CH2:25][CH:26]1[CH2:30][CH2:29][C:28](=O)[C:27]1([CH3:33])[CH3:32])[CH3:22].[B][B][B][B][B][B][B][B][B][B]>>[CH2:21]([O:23][C:24](=[O:34])[CH2:25][CH:26]1[CH2:30][CH2:29][CH:28]([NH:19][C:17]2[CH:16]=[CH:15][C:14]([F:20])=[C:13]([C@:4]3([CH3:12])[C:5]([CH3:10])([CH3:11])[C:6](=[O:9])[N:7]([CH3:8])[C:2]([NH2:1])=[N:3]3)[CH:18]=2)[C:27]1([CH3:33])[CH3:32])[CH3:22]

Participants

4

Reactant 3

HCID 10397833HCID 10397833, compoundHCID 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 57516116HCID 57516116, compound

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 rac-(2,2-dimethyl-3-oxo-cyclopentyl)-acetic acid ethyl ester (prepared according to Bunce, R. A. et al., J. Org. Chem. 1995, 60(9), 2748) using decaborane yielded a mixture of isomers of the title compound as a white foam. MS (ESI): m/z=461.3 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-27771483643b401583da6f48526bf176
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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