Dimethylformamide → HCID 46912985, compound

HRID 535982Notes

Reaction equation

HRID 535982 reaction equation
Cl[C:2]1[N:3]([CH2:26][CH2:27][CH3:28])[C:4](=[O:25])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=4[F:24])[CH:15]=3)=[N:8][C:9]=2[N:10]=1.C([O-])=O.[NH4+].CN(C=O)C>[Pd].O>[F:24][C:18]1[C:19]([F:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][N:14]1[CH:15]=[C:11]([C:7]2[NH:6][C:5]3[C:4](=[O:25])[N:3]([CH2:26][CH2:27][CH3:28])[CH:2]=[N:10][C:9]=3[N:8]=2)[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2723923Ammonium formateHCID 46912981HCID 46912981, compound

Product 1

HCID 46912985HCID 46912985, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
87.5 °C

Procedure

A mixture of 2-Chloro-8-[1-(2,3-difluoro-benzyl)-1H-pyrazol-4-yl]-1-propyl-1,7-dihydro-purin-6-one (0.04 g, 0.09 mmol), ammonium formate (0.134 g, 1.97 mmol), Pd\C (10%) (0.02 g), DMF (2 ml) and H2O (0.5 ml) were heated at 85-90° C. for 15 hours. Reaction mixture was cooled to 20-25° C. and then it was filtered through celite bed washed with methanol (10 ml). The filtrate was concentrated under vacuum. To this residue water (1 ml) was added and acidified with citric acid up to pH (1-2). Solid precipitated was filtered off and washed sequentially with cold water, diethyl ether to obtain pure 8-[1-(2,3-difluoro-benzyl)-1H-pyrazol-4-yl]-1-propyl-1,7-dihydro-purin-6-one (0.01 g, 28%) as a off white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. filtrationit was filtered through celite bed
  4. washwashed with methanol (10 ml)
  5. concentrationThe filtrate was concentrated under vacuum
  6. additionTo this residue water (1 ml) was added
  7. customSolid precipitated
  8. filtrationwas filtered off
  9. washwashed sequentially with cold water, diethyl ether

Sources & evidence

ORD record
ord-c8710535d7ce4cdaa82264e710478147
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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