2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine → 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)N4-((R)-8-fluorochroman-4-yl)pyrimidine-4,5-diamine

HRID 1363186Notes

Reaction equation

HRID 1363186 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][C@H:17]4[C:26]5[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=5)[O:20][CH2:19][CH2:18]4)[C:13]([N+:28]([O-])=O)=[CH:12][N:11]=3)[C:6]=2[CH:31]=1>CCOC(C)=O.[Pt]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][C@H:17]4[C:26]5[C:21](=[C:22]([F:27])[CH:23]=[CH:24][CH:25]=5)[O:20][CH2:19][CH2:18]4)[C:13]([NH2:28])=[CH:12][N:11]=3)[C:6]=2[CH:31]=1

Participants

4

Reactant 1

HCID 669704362-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine

Product 1

HCID 597049222-(6-fluoro-1H-benzo[d]imidazol-1-yl)N4-((R)-8-fluorochroman-4-yl)pyrimidine-4,5-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N—((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine in EtOAc (20 mL) was added 5 mol % of Platinum, 5% on activated carbon power, sulfide, 0.5% S (as sulfide) (45.6 mg). The mixture was sparged with argon, transferred to the Parr hydrogenation apparatus, then subjected to a purge/fill sequence with hydrogen (repeated 5×). The mixture was hydrogenated for 18 hr at 40 psi. Filtration through a pad of Celite and concentration of the filtrate gave crude 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)N4—((R)-8-fluorochroman-4-yl)pyrimidine-4,5-diamine that was carried on without further purification. MH+=425.

Workup

  1. customThe mixture was sparged with argon
  2. filtrationFiltration through a pad of Celite and concentration of the filtrate

Sources & evidence

ORD record
ord-ed4c7c0deba3499780851f94934ee4b2
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

Loading…