ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylate → HCID 178515237, compound

HRID 973541Notes

Reaction equation

HRID 973541 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[N:3]=1.O=[C:14]1[CH2:19][CH2:18][CH2:17][S:16][CH:15]1[C:20](OCC)=[O:21]>C(O)(=O)C.O>[N:7]1([C:4]2[N:3]=[C:2]3[NH:1][C:14]4[CH2:19][CH2:18][CH2:17][S:16][C:15]=4[C:20](=[O:21])[N:6]3[N:5]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylateHCID 137896925-(1-Piperidinyl)-1H-1,2,4-triazol-3-amine

Product 1

HCID 178515237HCID 178515237, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

16.7 g (0.1 mole) of 5-amino-3-piperidino-1H-1,2,4-triazole are dissolved in 10 ml of acetic acid and 18.8 g (0.1 mole) of ethyl 3-oxo-3,4,5,6-tetrahydro-2H-thiopyrane-2-carboxylate are added, then the reaction mixture is boiled for 10 minutes. The thick crystal mass thus obtained is diluted with 100 ml of water, the precipitated product is filtered off, washed with i-propanol and recrystallized from dimethylformamide. Thus 23.3 g (82.2%) of 2-piperidino-5,7,8,9-tetrahydrothiopyrano[3,2-d]-1,2,4-triazolo[1,5-a]pyrimidine-5(10H)-one are obtained with a melting point above 350° C.

Workup

  1. customThe thick crystal mass thus obtained
  2. filtrationthe precipitated product is filtered off
  3. washwashed with i-propanol
  4. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-38788ccf1ae143fa908e9ff8cad4b8fa
Source dataset
uspto-grants-1991_11
Patent number
US05064826

Reaction notes

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