Hydrochloric Acid → 5-(5-Chloromethyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo-[4,3-d]pyrimidin-7-one

HRID 21958Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH2:19][CH2:20][CH3:21])=[N:6][C:5]=2[C:4]([CH2:22][CH2:23][CH3:24])=[N:3]1.[ClH:25].[CH2:26]=O>O>[Cl:25][CH2:26][C:16]1[CH:15]=[CH:14][C:13]([O:18][CH2:19][CH2:20][CH3:21])=[C:12]([C:7]2[NH:8][C:9](=[O:11])[C:10]3[N:2]([CH3:1])[N:3]=[C:4]([CH2:22][CH2:23][CH3:24])[C:5]=3[N:6]=2)[CH:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-Methyl-5-(2-n-propoxyphenyl)-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (0.80 g, 0.00246 mol) was added portionwise to stirred concentrated hydrochloric acid (10 ml) at room temperature. Paraformaldehyde (0.20 g, 0.00246 mol) was then added and the resulting solution stirred at 120° C. for 22 hours. The reaction mixture was cooled and poured into ice and water (50 g), then the resulting mixture extracted with ethyl acetate (3×30 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum to give a white solid. Trituration with ether, followed by crystallisation from ethyl acetate-hexane, gave the title compound as colourless crystals (0.65 g, 70%), m.p. 102°-104° C. Found: C,60.91; H,6.14; N,14.94. C19H23CIN4O2 requires C,60.88; H,6.18; N,14.95%.

Workup

temperatureThe reaction mixture was cooled
extractionthe resulting mixture extracted with ethyl acetate (3×30 ml)
dry with materialdried (Na2SO4)
customevaporated under vacuum
customto give a white solid
customTrituration with ether, followed by crystallisation from ethyl acetate-hexane

Sources & evidence

ORD record: ord-1916abae3a88424fa1fab81bf4da47c3
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05426107

Reaction notes

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