Isopropylamine → HCID 18326419, compound

HRID 1250635Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH:13]([NH2:16])([CH3:15])[CH3:14]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:16][CH:13]([CH3:15])[CH3:14])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In DMF was dissolved 700 mg (3.2 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine, and then an aqueous solution of 443 mg (7.5 mmol) of isopropylamine was added dropwise to the resulting solution under ice cooling over 5 minutes. The reaction mixture was stirred at 0° C. for one hour and then allowed to resume room temperature, followed by stirring for one hour. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/6) to give 636 mg (yield: 82.4%) of the title compound.

Workup

customto resume room temperature
stirringby stirring for one hour
additionwas added to the reaction mixture
extractionfollowed by extraction with ethyl acetate (50 ml×3)
washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/6)

Sources & evidence

ORD record: ord-2186d0e01b6c4564b9b782ed876c3ac1
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339089B2

Reaction notes

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