Acetic Anhydride → HCID 135815269, compound

HRID 1977627Notes

Reaction equation

HRID 1977627 reaction equation
C(N(CC)CC)C.CN(C1C=CC=CN=1)C.C(O[C:21](=[O:23])[CH3:22])(=O)C.[NH2:24][C:25]1[CH:45]=[CH:44][C:28]([CH2:29][C:30]2[NH:31][C:32](=[O:43])[C:33]3[N:38]([CH3:39])[N:37]=[C:36]([CH2:40][CH2:41][CH3:42])[C:34]=3[N:35]=2)=[CH:27][CH:26]=1>ClCCl>[CH3:39][N:38]1[C:33]2[C:32](=[O:43])[NH:31][C:30]([CH2:29][C:28]3[CH:44]=[CH:45][C:25]([NH:24][C:21](=[O:23])[CH3:22])=[CH:26][CH:27]=3)=[N:35][C:34]=2[C:36]([CH2:40][CH2:41][CH3:42])=[N:37]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 1358152625-[(4-Aminophenyl)methyl]-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 135815269HCID 135815269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (160 μl, 0.0011 mol), dimethylaminopyridine (10 mg), and acetic anhydride (50 μl, 0.0005 mol) were added to a solution of 5-(4-aminobenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-7-one (110 mg, 0.00037 mol) in dichloromethane (9 ml). The resulting mixture was stirred overnight at room temperature under a nitrogen atmosphere. The mixture was then partitioned between 2M aqueous hydrochloric acid solution (15 ml) and dichloromethane (15 ml) and the aqueous phase extracted with dichloromethane/methanol (30 ml). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give, after crystallisation from ethyl acetate/methanol, the title compound as an off white solid (105 mg), m.p.272-275° C.

Workup

  1. customThe mixture was then partitioned between 2M aqueous hydrochloric acid solution (15 ml) and dichloromethane (15 ml)
  2. extractionthe aqueous phase extracted with dichloromethane/methanol (30 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give
  7. customafter crystallisation from ethyl acetate/methanol

Sources & evidence

ORD record
ord-677602eded614f208bad6d535fb17ecc
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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