O,O-Diethyl dithiophosphate → HCID 135730630, compound

HRID 354184Notes

Reaction equation

HRID 354184 reaction equation
[CH2:1]([O:5][C:6]1[C:13]([C:14]2[NH:15][C:16](=[O:27])[C:17]3[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=3)[N:19]=2)=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)[CH:2]([CH3:4])[CH3:3].P(S)(OCC)(OCC)=[S:29]>O.ClCCl>[CH2:1]([O:5][C:6]1[N:7]=[CH:8][C:9]([C:10](=[S:29])[NH2:11])=[CH:12][C:13]=1[C:14]1[NH:15][C:16](=[O:27])[C:17]2[C:18](=[C:20]([CH2:24][CH2:25][CH3:26])[N:21]([CH3:23])[N:22]=2)[N:19]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 9274O,O-Diethyl dithiophosphate2×HCID 135730601HCID 135730601, compound

Product 1

HCID 135730630HCID 135730630, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Water (2 drops) was added to a stirred suspension of 6-isobutoxy-5-(2-methyl-7-oxo-3-propyl-6,7-dihydro-2H-pyrazolo[4,3-d]pyrimidin-5-yl)-nicotinonitrile (Example 36) (150 mg, 0.41 mmol) in (EtO)2P(S)SH (0.5 mL). The mixture was stirred at room temperature. After 5 h more (EtO)2P(S)SH (0.5 mL) was added and dichloromethane (5 mL) added to aid stirring. After 14 h the reaction mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution. After filtration and separation of the phases the organics were washed again with saturated sodium bicarbonate solution and brine, dried (MgSO4) and concentrated. The product was purified by flash column chromatography (gradient elution from 100% dichloromethane to 96% dichloromethane:methanol) to give 80 mg product.

Workup

  1. stirringto aid stirring
  2. washwashed with saturated sodium bicarbonate solution
  3. filtrationAfter filtration and separation of the phases the
  4. washorganics were washed again with saturated sodium bicarbonate solution and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe product was purified by flash column chromatography (gradient elution from 100% dichloromethane to 96% dichloromethane:methanol)

Sources & evidence

ORD record
ord-c316c6e878f64d6f96aedc00c68b04bf
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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