Ammonia → 3-Benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine

HRID 636436Notes

Reaction equation

HRID 636436 reaction equation
[NH3:1].[C:2]1([S:8]([C:11]2[C:12]([S:24][CH3:25])=[N:13][N:14]3[C:19](Cl)=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.CN(C=O)C>[C:2]1([S:8]([C:11]2[C:12]([S:24][CH3:25])=[N:13][N:14]3[C:19]([NH2:1])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[N:16][C:15]=23)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 212549933-Benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 212550133-Benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamineYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

10 ml of a 50% solution of NH3 in MeOH was added to a solution of 0.50 g (1.3 mmol) of 3-benzenesulphonyl-7-chloro-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]-pyrimidine in 10 ml of DMF and stirred at RT for 2 hrs. The reaction solution was evaporated and the residue was partitioned between 2N NaOH and CH2Cl2. The aqueous phase was extracted three times with CH2Cl2, and the combined organic phases were dried (MgSO4), filtered and evaporated. Subsequent chromatography (SiO2, CH2Cl2/MeOH 10:1) and crystallization from EtOH yielded 0.38 g (80%) of 3-benzenesulphonyl-5-methoxymethyl-2-methylsulphanyl-pyrazolo[1,5-a]pyrimidin-7-ylamine as colorless crystals, m.p.>230°.

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was partitioned between 2N NaOH and CH2Cl2
  3. extractionThe aqueous phase was extracted three times with CH2Cl2
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customSubsequent chromatography (SiO2, CH2Cl2/MeOH 10:1) and crystallization from EtOH

Sources & evidence

ORD record
ord-d2a48ee7c4d4471e88347f3fed368de5
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

Loading…