Phosphorus oxychloride → 4-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidine
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]2[C:12](=O)[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=1.P(Cl)(Cl)([Cl:18])=O>O1CCOCC1>[Cl:18][C:12]1[C:13]2[NH:14][C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][C:8]=2[N:9]=[CH:10][N:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 6-(2-furyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-4-one (2.20 g) and phosphoryl chloride (10.7 g) was stirred at 100° C. for 20 min, dioxane (30 mL) was added, and the mixture was stirred at 100° C. for 3 hrs. After concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate-acetone (155 mL×4). The organic layers were combined, washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue washed with ethyl acetate-diethyl ether, and dried under reduced pressure at 60° C. to give the title compound (2.19 g).
Workup
- stirringthe mixture was stirred at 100° C. for 3 hrs
- concentrationAfter concentration under reduced pressure, saturated aqueous sodium hydrogen carbonate
- additionwas added to the residue
- extractionthe mixture was extracted with ethyl acetate-acetone (155 mL×4)
- washwashed with saturated brine (100 mL)
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- washThe residue washed with ethyl acetate-diethyl ether
- customdried under reduced pressure at 60° C.
Sources & evidence
- ORD record
- ord-60364eed59cf42df9902b300bf8ffe2b
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507740B2
Reaction notes
Loading…