3,4-Diaminopyridine → N-(4-amino-3-pyridinyl)-N'-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]thiourea

HRID 2248829Notes

Reaction equation

HRID 2248829 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:25]([NH:26][CH:27]3[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][N:35]=[C:36]=[S:37])[CH2:29][CH2:28]3)=[N:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:12][CH:11]=1>O1CCCC1>[NH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][C:3]=1[NH:8][C:36]([NH:35][CH2:34][CH2:33][N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:25]2[N:17]([CH2:16][C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=3)[C:18]3[C:23]([N:24]=2)=[CH:22][N:21]=[CH:20][N:19]=3)[CH2:28][CH2:29]1)=[S:37]

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 197852259-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-9H-purin-8-amine

Product 1

HCID 19785224N-(4-amino-3-pyridinyl)-N'-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.95 parts of 3,4-pyridinediamine, 16 parts of 9-[(4-fluorophenyl)methyl]-N-[1-(2-isothiocyanatoethyl)-4-piperidinyl]-9H-purin-8-amine, and 90 parts of tetrahydrofuran was stirred and refluxed overnight. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95/5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 10.5 parts of N-(4-amino-3-pyridinyl)-N'-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]thiourea (compound 182).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated

Sources & evidence

ORD record
ord-b4418bdf11744bf59a2eda7c09c68bf6
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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