Coumaranone → (6S)-2-amino-6-(5-(2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one

HRID 2409149Notes

Reaction equation

HRID 2409149 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:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23](=O)[CH2:22]1.[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:23]3[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:21][CH2:22]3)[CH:16]=[CH:15][C:14]=2[F:20])([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 23556CoumaranoneHCID 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 57497003(6S)-2-amino-6-(5-(2,3-dihydrobenzofuran-3-ylamino)-2-fluorophenyl)-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 2,3-dihydrobenzofuran-3-one using decaborane yielded a mixture of epimers of the title compound as a colorless waxy solid. MS (ESI): m/z=397.2 [M+H]+.

Workup

  1. customyielded

Sources & evidence

ORD record
ord-bf5efa44b25143d59e4864cf9a786970
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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