Ethyl 4-piperidinecarboxylate → Ethyl 1-[6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine-2-yl]-piperidine-4-carboxylate

HRID 366370Notes

Reaction equation

HRID 366370 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[S:8][C:6]=2[N:7]=1.[NH:23]1[CH2:28][CH2:27][CH:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]1>C(Cl)Cl>[CH3:11][C:9]1[S:8][C:6]2[N:7]=[C:2]([N:23]3[CH2:28][CH2:27][CH:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:25][CH2:24]3)[N:3]=[C:4]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:5]=2[CH:10]=1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 109585612-Chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno-[2,3-d]pyrimidine

Product 1

HCID 9846773Ethyl 1-[6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine-2-yl]-piperidine-4-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.67 g of 2-chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine and 3 g of ethyl piperidine-4-carboxylate are heated at 130° for 3 hours. After cooling, the residue is dissolved in methylene chloride and the solution is worked up in the customary manner. 0.5 g of ethyl 1-[6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine-2-yl]-piperidine-4-carboxylate is obtained.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-138540a02a0f4367be5c0c4b31587462
Source dataset
uspto-grants-2000_10
Patent number
US06130223

Reaction notes

Loading…