Sodium Carbonate → HCID 135815275, compound

HRID 1977639Notes

Reaction equation

HRID 1977639 reaction equation
C[O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[NH:9][C:10](=[O:21])[C:11]3[N:16]([CH3:17])[N:15]=[C:14]([CH2:18][CH2:19][CH3:20])[C:12]=3[N:13]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+]>Br>[OH:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[NH:9][C:10](=[O:21])[C:11]3[N:16]([CH3:17])[N:15]=[C:14]([CH2:18][CH2:19][CH3:20])[C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 135815268HCID 135815268, compound

Product 1

HCID 135815275HCID 135815275, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
130 °C

Procedure

60% w/w Hydrobromic acid (20 ml) was added to 5-(4-methoxybenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-7-one (630 mg) and the mixture stirred at 130° C. for 90 minutes. On cooling, the reaction was neutralized with saturated aqueous sodium carbonate solution and partitioned between dichloromethane (40 ml) and water (40 ml). The aqueous layer was further extracted with dichloromethane (100 ml), the combined organic layers dried (MgSO4), filtered and evaporated under reduced pressure. Crystallisation from ethyl acetate gave the title compound (75 mg), m.p.260° C.

Workup

  1. temperatureOn cooling
  2. custompartitioned between dichloromethane (40 ml) and water (40 ml)
  3. extractionThe aqueous layer was further extracted with dichloromethane (100 ml)
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customCrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-d00c49c35b234c67a7a225eb70f0e387
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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