Water → 6-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}hexanenitrile

HRID 1926877Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].[H-].[Na+].Cl[C:12]1[C:13]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[C:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:18][C:14]=2[N:15]=[CH:16][N:17]=1.O>CN(C=O)C>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[C:13]3[C:12]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])=[N:17][CH:16]=[N:15][C:14]=3[O:18][C:19]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Dissolve 850 mg (3.8 mmol) 6-hydroxyhexanenitrile [obtained according to Eur. J. Med. Chem. 36 (4), 303-311 (2001)] in 15 ml DMF, add, at 0° C., 180 mg 60% sodium hydride (dispersion in mineral oil; approx. 4.5 mmol) and stir the mixture for 1 h at room temperature. Next, add 1.26 g (3.8 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and stir the mixture overnight at 120° C. After cooling, add water to the mixture and extract with ethyl acetate. Dry the organic phase, and concentrate by evaporation. Purify the residue by flash chromatography on silica gel (solvent: cyclohexane/ethyl acetate 2:1→cyclohexane/ethyl acetate 1:2). 1.05 g (68% of theor.) of an orange-coloured oil is obtained, which is used as raw product in further reactions.

Workup

additionadd, at 0° C.
temperatureAfter cooling
extractionextract with ethyl acetate
customDry the organic phase
concentrationconcentrate by evaporation
customPurify the residue by flash chromatography on silica gel (solvent: cyclohexane/ethyl acetate 2:1→cyclohexane/ethyl acetate 1:2)
custom1.05 g (68% of theor.) of an orange-coloured oil is obtained

Sources & evidence

ORD record: ord-e8380b195eb74c3ab46697e344e8f38c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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