Ethanol → HCID 391851, compound

HRID 371458Notes

Reaction equation

HRID 371458 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([NH2:23])=[N:17][C:18]([NH2:22])=[N:19][C:20]=3[CH3:21])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#N.S(=O)(=O)(O)[OH:25].[CH2:29]([OH:31])[CH3:30]>>[NH2:22][C:18]1[N:17]=[C:16]([NH2:23])[C:15]([N:12]2[CH2:13][CH2:14][N:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]([O:31][CH2:29][CH3:30])=[O:25])=[CH:8][CH:7]=3)[CH2:10][CH2:11]2)=[C:20]([CH3:21])[N:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 391850HCID 391850, compound

Product 1

HCID 391851HCID 391851, compound

Conditions

Temperature
130 °C

Procedure

A mixture of 5.0 g (0.016 mole) of 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-methyl-2,4-pyrimidinediamine, 30 ml of 95% ethanol and 30 ml of sulfuric acid was heated under reflux at 130° C. for four hours and cooled. The solution was poured into 400 g of ice. The solid was collected, washed first with 5N aqueous sodium carbonate solution and then with 50 ml of water. Recrystallization from N,N-dimethylformamide gave 1.72 g of the product as an off-white solid, mp 281°-285° C.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. customThe solid was collected
  4. washwashed first with 5N aqueous sodium carbonate solution
  5. customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-ce4899f83c0143f29e8c04c044ada4e5
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

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