Formamide → HCID 15858662, compound

HRID 362298Notes

Reaction equation

HRID 362298 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:21]#[N:22])=[C:11]([NH2:20])[N:12]([C:14]3C=CC=CC=3)[CH:13]=2)[CH:6]=[CH:7][CH:8]=1.CN([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28]N=1)C.O.[CH:33]([NH2:35])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[C:11]([NH2:20])=[N:12][CH:14]=[N:22][C:21]=3[N:35]([C:33]3[CH:26]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:13]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 218852-DimethylaminopyridineHCID 54418446HCID 54418446, compound

Product 1

HCID 15858662HCID 15858662, compound

Procedure

1.27 g of 4-(3-methoxyphenyl)-1-phenyl-2-amino-3-cyanopyrrole are heated at 180° C. with a spatula tipful of dimethylaminopyridine for 7 h in 14 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 (ethyl acetate/hexane 4:1), the product-containing fractions are concentrated, slurried in ether and filtered. 5-(3-Methoxyphenyl)-7-phenyl-4-aminopyrrolo[2,3-d]pyrimidine having a melting point of 159°-160° C. is obtained. 1H--NMR (d6 -DMSO): delta (ppm)=3.8 (s, 3H), 6.3 (br. s, 2H), 6.9 (br. d, 1H), 7.1 (m, 2H), 7.3-7.45 (m, 2H), 7.55(t, 2H), 7.75 (s, 1H), 7.9 (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 (ethyl acetate/hexane 4:1), the product-containing fractions are concentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-50754a46cd4d41c299d2dcf6fbb5a388
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

Loading…