2,4-Dimethoxybenzonitrile → 1H-Purine, 8-(2,4-dimethoxyphenyl)-

HRID 1155063

Reaction equation

[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[C:13]#N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[C:13]1[NH:8][C:7]2[C:2](=[N:3][CH:4]=[N:5][CH:6]=2)[N:1]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2 g of 4,5-diamino-pyrimidine, 4 g of 2,4-dimethoxy-benzonitrile, 6 g of p-toluene sulfonic acid hydrate, and 40 ml of benzene was heated, whereby the benzene was distilled off. The residue was heated for 30 minutes at 120° C. After cooling the residue was triturated with 2 N ammonia and extracted with ethyl acetate. The ethyl acetate phase was extracted with 2 N hydrochloric acid, the aqueous phase was neutralized and again extracted with ethyl acetate, and subsequently the organic phase was extracted with 2 N sodium hydroxide solution. When the aqueous phase was neutralized, the product was precipitated and recrystallized from water.

Workup

temperaturewas heated
distillationwhereby the benzene was distilled off
temperatureAfter cooling the residue
customwas triturated with 2 N ammonia
extractionextracted with ethyl acetate
extractionThe ethyl acetate phase was extracted with 2 N hydrochloric acid
extractionagain extracted with ethyl acetate
extractionsubsequently the organic phase was extracted with 2 N sodium hydroxide solution
customthe product was precipitated
customrecrystallized from water

Sources & evidence

ORD record: ord-63f0d60977ab4bd0987398e8ee4f424a
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04299834

Linked notes

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