Ammonium formate → HCID 77105602, compound

HRID 2201175Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[N:13]([C:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:15]3[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[O:24])[N:18]([CH3:25])[C:16]3=2)[CH2:12][CH2:11][CH:10]=1.C([O-])=O.[NH4+]>[Pd].CCO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:17]2[N:13]([C:14]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:15]3[C:21](=[O:22])[N:20]([CH3:23])[C:19](=[O:24])[N:18]([CH3:25])[C:16]3=2)[CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

10-(2,3-Difluorophenyl)-1,3-dimethyl-5-phenyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione (step 1,) (40 mg, 0.095 mmol), 10% wt. palladium on activated carbon (10 mg, 9.54 μmol) and ammonium formate (30.1 mg, 0.477 mmol) were suspended in EtOH (5 mL) and the mixture stirred at 50° C. for 19 hours, adding extra 10% wt. palladium on activated carbon (10 mg, 9.54 μmol) after 17 hours. The reaction mixture was cooled to RT and filtered through a Celite® (filter material) cartridge (10 g), rinsing the residues with MeOH. The filtrates were evaporated under reduced pressure. The residue was partitioned between DCM and water and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated under reduced pressure to afford the title product as a pale yellow oil.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered through a Celite® (filter material) cartridge (10 g)
washrinsing the residues with MeOH
customThe filtrates were evaporated under reduced pressure
customThe residue was partitioned between DCM and water
customthe phases separated
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-1007a1b33c574932ac043e070d88e517
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359381B2

Reaction notes

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