Formamide → 7-(4-Chlorophenyl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 903851Notes

Reaction equation

HRID 903851 reaction equation
[NH2:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:4]([CH3:10])=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[CH:18]([NH2:20])=O>CN(C)C=O.C(O)=O>[NH2:8][C:7]1[C:6]2[C:5]([CH3:9])=[C:4]([CH3:10])[N:3]([C:11]3[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=3)[C:2]=2[N:1]=[CH:18][N:20]=1

Participants

5

Reactant 2

HCID 713FormamideHCID 8027198HCID 8027198, compound

Product 1

HCID 49623717-(4-Chlorophenyl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

15 g (0.06 mol) of 2-amino-1-(4-chlorophenyl)-3-cyano-4,5-dimethylpyrrole in 100 ml of formamide, 30 ml of dimethylformamide and 15 ml of concentrated formic acid are heated under reflux for 7 hours. The crystals which precipitate on cooling are washed with water and recrystallised from ethanolic potassium hydroxide solution. Melting point: 250° C., yield: 13 g (79% of theory).

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe crystals which precipitate
  3. temperatureon cooling
  4. washare washed with water
  5. customrecrystallised from ethanolic potassium hydroxide solution

Sources & evidence

ORD record
ord-e200a253a2ba48d3990917afbef69fce
Source dataset
uspto-grants-1980_10
Patent number
US04229453

Reaction notes

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