Dodecylamine → 2-Chloro-4-dodecylamino-7-methylthieno[3,2-d]pyrimidine

HRID 1250692Notes

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.[CH2:13]([NH2:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:25][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In 1 ml of DMF, 700 mg (3.2 mmol) of 2,4-dichloro-7-methylthieno[3,2-d]pyrimidine was dissolved, and then 1.30 g (7.0 mmol) of dodecylamine was added dropwise thereto over 5 minutes. The reaction solution was stirred at 0° C. for one hour and then allowed to resume room temperature, followed by stirring for further 1 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=1/10) to give 745 mg (yield: 63.4%) of the title compound.

Workup

customto resume room temperature
stirringby stirring for further 1 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=1/10)

Sources & evidence

ORD record: ord-bddd7c034eef4f0589c4827665487ce3
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339089B2

Reaction notes

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