4-Nitrophenol → 6-(4-Benzyloxyphenyl)-4-(4-nitrophenoxy)-7H-pyrrolo[2,3-d]pyrimidine

HRID 853463Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[NH:45][C:39]3[N:40]=[CH:41][N:42]=[C:43](Cl)[C:38]=3[CH:37]=2)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[NH:45][C:39]3[N:40]=[CH:41][N:42]=[C:43]([O:21][C:18]4[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=4)[C:38]=3[CH:37]=2)=[CH:32][CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 130 °C

Procedure

After adding 2.97 of potassium carbonate and 30 ml of dimethylformamide to 3.09 g of 4-nitrophenol and stirring the mixture at 130° C. for 10 minutes, 2.49 g of 6-(4-benzyloxyphenyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine was added and the mixture was further stirred at 130° C. for 5 hours and at 135° C. overnight. After returning the mixture to room temperature, water was added, the precipitated solid was filtered out and subjected to NH silica gel column chromatography (ethyl acetate) and silica gel column chromatography (ethyl acetate), and then ether and ethyl acetate were added prior to sonication. The solid was filtered out to obtain 1.2 g of the title compound.

Workup

stirringthe mixture was further stirred at 130° C. for 5 hours and at 135° C. overnight
customto room temperature
filtrationthe precipitated solid was filtered out
additionether and ethyl acetate were added
customto sonication
filtrationThe solid was filtered out

Sources & evidence

ORD record: ord-baaca569bd0a424cad0fed2c45c7d1cd
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253286B2

Reaction notes

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