Urea → HCID 178517326, compound

HRID 1904858Notes

Reaction equation

HRID 1904858 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]3[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:21]4[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=4[N:19]=3)[CH2:13][CH2:12]2)[C:3]=1[NH2:35].N[C:37](N)=[O:38]>O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:35]=[C:37]([OH:38])[N:8]2[CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][C:18]2[N:22]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)[C:21]3[CH:31]=[CH:32][CH:33]=[CH:34][C:20]=3[N:19]=2)[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 1176UreaHCID 14518070HCID 14518070, compound

Product 1

HCID 178517326HCID 178517326, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 7.5 parts of 6-chloro-N4 -[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-4,5-pyrimidinediamine and 3.6 parts of urea was stirred and heated for 20 minutes at 220° C. Water was added to the reaction mixture. The precipitated product was filtered off and crystallized from methanol. The product was filtered off and recrystallized from a mixture of N,N-dimethylformamide and methanol, yielding 2.5 parts (32%) of 6-chloro-9-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-9H-purin-8-ol; mp. 243.0° C. (494).

Workup

  1. filtrationThe precipitated product was filtered off
  2. customcrystallized from methanol
  3. filtrationThe product was filtered off
  4. customrecrystallized from a mixture of N,N-dimethylformamide and methanol

Sources & evidence

ORD record
ord-006cc5f4c3eb41009382b4d471095c40
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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