Methanesulfonyl chloride → 5-(2-Ethoxy-5-methanesulphonamidophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 327060Notes

Reaction equation

HRID 327060 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:27][CH2:28][CH3:29])=[C:11]([C:13]2[NH:14][C:15](=[O:26])[C:16]3[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=3[N:18]=2)[CH:12]=1>N1C=CC=CC=1>[CH2:28]([O:27][C:10]1[CH:9]=[CH:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:12][C:11]=1[C:13]1[NH:14][C:15](=[O:26])[C:16]2[N:21]([CH3:22])[N:20]=[C:19]([CH2:23][CH2:24][CH3:25])[C:17]=2[N:18]=1)[CH3:29]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 1357385605-(5-Amino-2-ethoxyphenyl)-1-methyl-3-propyl-1,4-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Product 1

HCID 1357385525-(2-Ethoxy-5-methanesulphonamidophenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (0.157 g, 0.00137 mol) was added to a stirred solution of 5-(5-amino-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (0.45 g, 0.00137 mol) in dry pyridine (30 ml) at 0° C. The mixture was stirred for 18 hours at room temperature and then evaporated under vacuum. The residue was suspended in saturated aqueous sodium bicarbonate solution (50 ml) and the mixture extracted with dichloromethane (2×30 ml). The organic extracts were combined, washed with brine (2×30 ml), dried (Na2SO4) an evaporated under vacuum. The residue was triturated with ether, chromatographed on silica gel (12 g), eluting with a 98.5:1.5 mixture of dichloromethane and methanol, and the required product crystallised form ethyl acetate-hexane to give the title compound as a white powder (0.32 g, 58%), m.p. 205°-206° C. Found: C,53.63; H,5.66; N,17.24. C18H23N5O4S requires C,53.32; H,5.72; N,17.27%.

Workup

  1. customevaporated under vacuum
  2. extractionthe mixture extracted with dichloromethane (2×30 ml)
  3. washwashed with brine (2×30 ml)
  4. dry with materialdried (Na2SO4)
  5. customan evaporated under vacuum
  6. customThe residue was triturated with ether
  7. customchromatographed on silica gel (12 g)
  8. washeluting with a 98.5:1.5 mixture of dichloromethane and methanol
  9. customthe required product crystallised
  10. customform ethyl acetate-hexane

Sources & evidence

ORD record
ord-f3ab16314c6b44ea9822a2a8947cb89e
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

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