Diisopropylethylamine → Methyl 6-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]hexanoate

HRID 1926871

Reaction equation

Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(C(C)C)C(C)C.Cl.[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35]>CN(C=O)C>[CH3:27][O:28][C:29](=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Heat 2.0 g (8.67 mmol) 4-chloro-6-phenylfuro[2,3-d]pyrimidine and 6.04 ml (34.7 mmol) DIEA in 5 ml DMF to 160° C. Add 3.15 g (17.34 mmol) 6-aminohexanoic acid methyl ester hydrochloride and stir for 4 h at 160° C. After cooling, add the mixture to ice water and extract three times with ethyl acetate. Combine the organic phases and wash with saturated ammonium chloride solution, dry over magnesium sulphate and concentrate under vacuum. Add methanol to the oil residue. Filter off the precipitated solid with suction, wash with methanol again and dry the solid at high vacuum. 1.85 g (57.2% of theor.) of the target compound is obtained.

Workup

temperatureAfter cooling
extractionextract three times with ethyl acetate
washwash with saturated ammonium chloride solution
dry with materialdry over magnesium sulphate
concentrationconcentrate under vacuum
filtrationFilter off the precipitated solid with suction
washwash with methanol again
customdry the solid at high vacuum
custom1.85 g (57.2% of theor.) of the target compound is obtained

Sources & evidence

ORD record: ord-5cdc9941b0684131bd89d6c7c9fe9ad1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Linked notes

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