Ethyl 4-isothiocyanatopiperidine-1-carboxylate → Ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylate

HRID 256642Notes

Reaction equation

HRID 256642 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:13]([NH2:14])=[CH:12][N:11]=[CH:10][N:9]=1.[N:15]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]1)=[C:16]=[S:17]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[C:13]([NH:14][C:16]([NH:15][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)=[S:17])=[CH:12][N:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 3018454Ethyl 4-isothiocyanatopiperidine-1-carboxylateHCID 70462932N4-(2-furanylmethyl)-4,5-pyrimidinediamine

Product 1

HCID 19785223Ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 42.5 parts of N4 -(2-furanylmethyl)-4,5-pyrimidinediamine, 50.5 parts of ethyl 4-isothiocyanato-1-piperidinecarboxylate and 630 parts of tetrahydrofuran was stirred for 48 hours at reflux temperature. After cooling, the product was filtered off, washed with tetrahydrofuran and 1,1'-oxybisethane and dried, yielding 86.4 parts (96.2%) of ethyl 4-[[[[4-[(2-furanylmethyl)amino]-5-pyrimidinyl]amino]thioxomethyl]-amino]-1-piperidinecarboxylate (interm. 31).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe product was filtered off
  4. washwashed with tetrahydrofuran and 1,1'-oxybisethane
  5. customdried

Sources & evidence

ORD record
ord-37db89f323564c00a4ef7b0370897e5e
Source dataset
uspto-grants-1993_11
Patent number
US05258380

Reaction notes

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