Ammonia → 4-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine

HRID 1926885Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16](=O)[NH:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][CH:4]=1)[CH3:2].P(Cl)(Cl)([Cl:27])=O.N>O>[Cl:27][C:16]1[C:17]2[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=3)=[C:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:11][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Put 72 g (227.6 mmol) 5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4(3H)-one in 360 ml (4.6 mol) phosphoryl chloride and heat to reflux. Stir the mixture for approx. 1 h at 120° C., before adding the reaction mixture dropwise, after cooling to RT, at controlled dose and with vigorous stirring, to a mixture of 2.2 litres of 25% ammonia solution and 1.2 litres water (pH>9, temperature 55-75° C.). Extract the aqueous mixture three times with dichloromethane, combine the organic phases, dry over sodium sulphate and concentrate by vacuum evaporation. Wash the residue with a little diisopropyl ether, and after filtration and drying at high vacuum, 66.1 g (85.2% of theor.) of the target product is obtained.

Workup

additionbefore adding the reaction mixture dropwise
extractionExtract the aqueous mixture three times with dichloromethane
dry with materialdry over sodium sulphate
concentrationconcentrate by vacuum evaporation
washWash the residue with a little diisopropyl ether
filtrationafter filtration
customdrying at high vacuum, 66.1 g (85.2% of theor.) of the target product
customis obtained

Sources & evidence

ORD record: ord-9d4c79e5faf540f49e6e6242e4cba913
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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