3,4-Dinitrophenol → 4-(3,4-dinitro-phenoxy)-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidine

HRID 491653Notes

Reaction equation

HRID 491653 reaction equation
Cl[C:2]1[CH:3]2[CH:10]=[CH:9][NH:8][CH:4]2[N:5]=[CH:6][N:7]=1.[N+:11]([C:14]1[CH:15]=[C:16]([OH:23])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])([O-:13])=[O:12]>>[N+:11]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[O:23][C:2]1[CH:3]2[CH:10]=[CH:9][NH:8][CH:4]2[N:5]=[CH:6][N:7]=1)([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 113483,4-DinitrophenolHCID 690208364-chloro-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 865946914-(3,4-dinitro-phenoxy)-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidine

Procedure

4-Chloro-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidine (1.66 g, 10.8 mmol), 3,4-dinitrophenol (2.4 g, 13 mmol) and TFA/TEA were heated at 150° C. for 2 h. The resulting green solid was purified on silica gel using a Hexane/EtOAc gradient (100/0 to 50/50) to give 4-(3,4-dinitro-phenoxy)-7,7a-dihydro-4aH-pyrrolo[2,3-d]pyrimidine.

Workup

  1. customThe resulting green solid was purified on silica gel using a Hexane/EtOAc gradient (100/0 to 50/50)

Sources & evidence

ORD record
ord-75279a31f82045f288298f8789a87447
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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