Formic Acid → HCID 70202600, compound

HRID 362305Notes

Reaction equation

HRID 362305 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:11]([C:25]#[N:26])=[C:12]([NH2:24])[N:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17](OCC)[CH:16]=4)[CH:14]=3)=[CH:4][C:3]=2O1.[CH:27]([OH:29])=O.[CH3:30][N:31](C=O)C.[OH2:35].[CH:36](N)=O>>[CH2:1]1[O:9][C:8]2[CH:3]=[CH:4][C:5]([C:10]3[C:11]4[C:25]([NH2:26])=[N:31][CH:30]=[N:24][C:12]=4[N:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:29][CH2:27][CH3:36])[CH:16]=4)[CH:14]=3)=[CH:6][C:7]=2[O:35]1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 713FormamideHCID 962WaterHCID 6228DimethylformamideHCID 53982478HCID 53982478, compound

Product 1

HCID 70202600HCID 70202600, compound

Procedure

0.8 g of 4-(3,4-methylenedioxyphenyl)-1-(3-ethoxyphenyl)-2-amino-3-cyanopyrrole is heated at 160° C. for 6 h in a mixture of 8 ml of formamide, 4 ml of formic acid and 1.5 ml of DMF. 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 (EA/hexane 3:4), the product-containing fractions are concentrated, slurried in ether and filtered. After repeated chromatography on silica gel (methylene chloride/methanol containing NH3 (4N) 97:3), the product-containing fractions are concentrated. The residue is slurried with ether/EA and the crystals are filtered off. 5-(3,4-Methylenedioxyphenyl)-7-(3-ethoxyphenyl)-4-aminopyrrolo-[2,3-d]pyrimidine having a melting point of 153°-155° C. is obtained. 1H--NMR (d6 -DMSO): delta (ppm)=1.35 (t, 3H), 4.1 (q, 2H), 6.1 (s, 2H), 6.25 (br. s, 2H), 6.9 br. d, 1H), 7.0 (m, 2H), 7.1 (s, 1H), 7.4-7.5 (m, 3H), 7.7 (s, 1H), 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 (EA/hexane 3:4), the product-containing fractions are concentrated
  6. filtrationfiltered
  7. concentrationthe product-containing fractions are concentrated
  8. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-392edd6dfb6b434186863349600e1246
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

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