Formamide → HCID 44385080, compound

HRID 362297Notes

Reaction equation

HRID 362297 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.CN([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27]N=1)C.O.[CH:32]([NH2:34])=O>>[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 218852-DimethylaminopyridineHCID 54496557HCID 54496557, compound

Product 1

HCID 44385080HCID 44385080, compound

Procedure

1 g of 4-(3-chlorophenyl)-1-phenyl-2-amino-3-cyanopyrrole is heated at 180° C. with a spatula tipful of dimethylaminopyridine for 14 h in 10 ml of formamide under a nitrogen atmosphere. After cooling to RT, the mixture is treated with water and the crystals obtained are filtered off, washed with water and dried. After chromatography on silica gel (methylene chloride/methanol 15:1), the product-containing fractions are concentrated, slurried in ether and filtered. 5-(3-Chlorophenyl)-7-phenyl-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 173°-175° C. is obtained. 1H--NMR (d6 -DMSO): delta (ppm)=6.3 (br. s, 2H), 7.3-7.55 (m, 6H), 7.65(s, 1H), 7.8 (s, 1H), 7.85 (d, 2H), 8.2 (s, 1H).

Workup

  1. customthe crystals obtained
  2. filtrationare filtered off
  3. washwashed with water
  4. customdried
  5. concentrationAfter chromatography on silica gel (methylene chloride/methanol 15:1), the product-containing fractions are concentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a05aaf06f1374308b228ba7c1ab9eed0
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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