HCID 13974581, compound → HCID 66727426, compound

HRID 2409173Notes

Reaction equation

HRID 2409173 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.O=[C:22]1[CH2:27][CH:26]2[CH2:28][CH:23]1[CH2:24][CH:25]2[O:29][C:30](=[O:32])[CH3:31].[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:22]3[CH2:27][CH:26]4[CH2:28][CH:23]3[CH2:24][CH:25]4[O:29][C:30](=[O:32])[CH3:31])[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 13974581HCID 13974581, 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 66727426HCID 66727426, 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-acetic acid 5-oxo-bicyclo[2.2.1]hept-2-yl ester (prepared as in J. Meinwald et al., Tetrahedron 1962, 18, 815-820) using decaborane yielded a mixture of isomers of the title compound as a white foam. MS (ESI): m/z=431.4 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-7e5664eb777f492291a8c5f2cdb8d71a
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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