Methyl isothiocyanate → N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]-N'-methylthiourea

HRID 2248827Notes

Reaction equation

HRID 2248827 reaction equation
[N:1]([CH3:4])=[C:2]=[S:3].[NH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:16]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[C:17]3[C:22]([N:23]=2)=[CH:21][N:20]=[CH:19][N:18]=3)[CH2:10][CH2:9]1>O1CCCC1>[F:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:16]2[C:15]([NH:14][CH:11]3[CH2:10][CH2:9][N:8]([CH2:7][CH2:6][NH:5][C:2]([NH:1][CH3:4])=[S:3])[CH2:13][CH2:12]3)=[N:23][C:22]3[C:17]2=[N:18][CH:19]=[N:20][CH:21]=3)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 19785318N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine

Product 1

HCID 19785234N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]-N'-methylthioureaYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.7 parts of isothiocyanatomethane, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine and 90 parts of tetrahydrofuran was stirred for 4 hours at room temperature. After evaporation, 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 first fraction was collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.3 parts (29%) of N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]-N'-methylthiourea; mp. 205.5° C. (compound 179).

Workup

  1. customAfter evaporation
  2. customthe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe first fraction was collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-0a76f5d407534870a4b0570913640445
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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