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

HRID 21945Notes

Reaction equation

HRID 21945 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) and 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 from 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. customevaporated 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 from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4a1604600d37463eba61fa4900b47dcf
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

Loading…