Formic Acid → 6-(4-nitrophenyl)-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one

HRID 567765Notes

Reaction equation

HRID 567765 reaction equation
[NH2:1][C:2]1[NH:3][C:4]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:5][C:6]=1[C:7]([O:9]CC)=O.[CH:21]([NH2:23])=O.CN(C=O)C.C(O)=O>C(O)(C)C>[OH:9][C:7]1[C:6]2[CH:5]=[C:4]([C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)[NH:3][C:2]=2[N:1]=[CH:21][N:23]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 713FormamideHCID 6228DimethylformamideHCID 21262647Ethyl 2-amino-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 1785265146-(4-nitrophenyl)-1,7-dihydropyrrolo[2,3-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.5 g (97 mmol) of 2-amino-3-ethoxycarbonyl-5-(4-nitrophenyl)pyrrole, 19.4 ml of formamide, 9.7 ml of DMF and 3.1 ml of formic acid are stirred at 150° C. together for 22 h. 1 ml of isopropanol is added to the warm reaction mixture. After cooling the reaction mixture, the precipitated product is filtered off. It is washed successively three times with 10 ml of ethanol each time, twice with 10 ml of isopropanol each time and twice with 10 ml of hexane each time. 4-Hydroxy-6-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine is obtained as rust-brown crystals which are employed for the next stage; MS: (M)+=256.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe precipitated product is filtered off
  3. washIt is washed successively three times with 10 ml of ethanol each time

Sources & evidence

ORD record
ord-1a3181e1a8fd47a5a1aacc06178e88dd
Source dataset
uspto-grants-2001_01
Patent number
US06180636B2

Reaction notes

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