Formamide → HCID 11558549, compound

HRID 362299Notes

Reaction equation

HRID 362299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]#[N:21])=[C:10]([NH2:19])[N:11]([C:13]3C=CC=CC=3)[CH:12]=2)=[CH:4][CH:3]=1.CN([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]N=1)C.O.[CH:32]([NH2:34])=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[C:10]([NH2:19])=[N:11][CH:13]=[N:21][C:20]=3[N:34]([C:32]3[CH:25]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 218852-DimethylaminopyridineHCID 11708901HCID 11708901, compound

Product 1

HCID 11558549HCID 11558549, compound

Procedure

4.78 g of 4-(4-fluorophenyl)-1-phenyl-2-amino-3-cyanopyrrole are heated at 180° C. with a spatula tipful of dimethylaminopyridine for 3.5 h in 50 ml of formamide under a nitrogen atmosphere. After cooling to RT, the mixture is treated with water and extracted 3 times with EA. The organic phases are washed with water, dried over Na2SO4 and concentrated. The residue is slurried with EA/ether and the crystals are filtered off. The crystals are suspended in hot ethanol and filtered off after cooling to RT. 5-(4-Fluorophenyl)-7-phenyl-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 202°-203° C. is obtained. 1H--NMR (d6 -DMSO): delta (ppm)=6.3 (br. s, 2H), 7.3-7.4 (m, 3H), 7.5-7.65 (m, 4H), 7.75 (s, 1H), 7.85 (d, 2H), 8.2 (s,1H).

Workup

  1. extractionextracted 3 times with EA
  2. washThe organic phases are washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. filtrationthe crystals are filtered off
  6. filtrationfiltered off
  7. temperatureafter cooling to RT

Sources & evidence

ORD record
ord-ca0c39370b294c698e37dd6c725ba7d8
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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