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

HRID 369709Notes

Reaction equation

HRID 369709 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-nitro-phenyl)-pyrrole, 19.4 ml of formamide, 9.7 ml of DMF and 3.1 ml of formic acid are stirred together at 150° C. for 22 hours. 1 ml of isopropanol is added to the warm reaction mixture. After the reaction mixture has cooled, the precipitated product is filtered off and washed in succession 3 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. The title compound is obtained in the form of rust-brown crystals which are used for the next step; MS: (M)+ =256.

Workup

  1. temperatureAfter the reaction mixture has cooled
  2. filtrationthe precipitated product is filtered off
  3. washwashed in succession 3 times with 10 ml of ethanol each time

Sources & evidence

ORD record
ord-ff87f2aec3c346ab85e56db946f26d20
Source dataset
uspto-grants-2000_10
Patent number
US06140317

Reaction notes

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