HCID 67063098, compound → HCID 67063019, compound

HRID 599273Notes

Reaction equation

HRID 599273 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14](SC)=[N:15][CH:16]=3)[N:11]([CH3:21])[C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[F:8]>C1COCC1.[Ni]>[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][CH:14]=[N:15][CH:16]=3)[N:11]([CH3:21])[C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 67063098HCID 67063098, compound

Product 1

HCID 67063019HCID 67063019, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example A1 (700 mg, 2.2 mmol) in THF (10 mL) was added Raney-Ni (50% wt slurry in water, 1.0 g) and then the reaction mixture was stirred under 1 atm of H2 at 60° C. for 5 h. The mixture was filtered through diatomite and the cake was washed with THF. The combined filtrate was concentrated to give 3-(3-amino-4-fluoro-phenyl)-1-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (460 mg, 76% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.77 (s, 1 H), 8.39 (s, 1 H), 6.99 (dd, J=11.4, 8.7 Hz, 1 H), 6.72 (d, J=8.1 Hz, 1 H), 6.49 (m, 1 H), 5.24 (br s, 2 H), 4.73 (s, 2 H), 3.28 (s, 3 H). MS (ESI) m/z: 274.2 (M+H+).

Workup

  1. filtrationThe mixture was filtered through diatomite
  2. washthe cake was washed with THF
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-99b171c371de4053935f6b73cdf37f61
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…