Acetic Acid → 2-methylthio-5,6,7,9-tetrahydrothiopyrano[3,4-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one

HRID 973544Notes

Reaction equation

HRID 973544 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.O=[C:10]1[CH:15]([C:16](OCC)=O)[CH2:14][CH2:13][S:12][CH2:11]1.C(O)(=[O:23])C>>[CH3:8][S:7][C:4]1[N:3]=[C:2]2[N:1]=[C:14]3[C:13](=[O:23])[S:12][CH2:11][CH:10]=[C:15]3[CH2:16][N:6]2[N:5]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 784713-(Methylthio)-1,2,4-triazol-5-amineHCID 15049900Ethyl 3-oxothiane-4-carboxylate

Product 1

HCID 199886062-methylthio-5,6,7,9-tetrahydrothiopyrano[3,4-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-oneYield 62.9%

Procedure

0.976 g (0.0075 mole) of 5-amino-3-methylthio-1H-1,2,4-triazole are dissolved in 6 ml of acetic acid, then 1.368 g (0.075 mole) of ethyl 3-oxo-3,4,5,6-tetrahydro-2H-thiopyrane-4-carboxylate are added and the reaction mixture is boiled for 30 minutes. The precipitated product is filtered off from the hot solution, washed with water and recrystallized from dimethylformamide. Thus 1.2 g (62.9%) of 2-methylthio-5,6,7,9-tetrahydrothiopyrano[3,4-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained which melt at 294°-297° C.

Workup

  1. filtrationThe precipitated product is filtered off from the hot solution
  2. washwashed with water
  3. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-31cd5683d5e74ad18d5d2d1373a505dc
Source dataset
uspto-grants-1991_11
Patent number
US05064826

Reaction notes

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