Diethyl acetylenedicarboxylate → ethyl 2-piperidino-7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylate

HRID 1278325Notes

Reaction equation

HRID 1278325 reaction equation
[NH2:1][C:2]1[S:3][C:4]([N:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:5][N:6]=1.[C:13]([C:20](OCC)=[O:21])#[C:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[N:7]1([C:4]2[S:3][C:2]3=[N:1][C:20](=[O:21])[CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:6]3[N:5]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 15000105-Piperidin-1-yl-1,3,4-thiadiazol-2-amine

Product 1

HCID 12899660ethyl 2-piperidino-7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The procedure used was as described in Example 5. However, there were used 9.2 g of 2-amino-5-piperidino-1,3,4-thiadiazole, 8.5 g of diethyl acetylenedicarboxylate and 200 ml of ethanol. Thus 9.8 g (63.7% of the theoretical yield) of ethyl 2-piperidino-7H-1,3,4-thiadiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylate, melting at 125° to 127° C., were obtained.

Sources & evidence

ORD record
ord-a88212953d824c88aa45b93e3d6abcb0
Source dataset
uspto-grants-1981_07
Patent number
US04281120

Reaction notes

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