N,N-Dimethylaniline → 4-Chloro-6-cyclopentylpyrimidin-2-amine
Reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[CH:5]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:25])=O>[Cl-].C([N+](CC)(CC)CC)C.C(#N)C>[NH2:1][C:2]1[N:7]=[C:6]([Cl:25])[CH:5]=[C:4]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1Participants
6
Conditions
- Temperature
- 110 °C
Procedure
A suspension of 2-amino-6-cyclopentyl-3H-pyrimidin-4-one (1.52 g, 8.4 mmol), tetraethyl ammonium chloride (2.8 g 16.9 mmol) and dimethylaniline (1.1 mL, 8.4 mmol) in acetonitrile (16 mL) was treated with phosphorous oxychloride (4.7 mL, 51 mmol) and heated at 110° C. for 20 min. The resulting solution was cooled to rt and concentrated to minimum volume then diluted with CHCl3 and ice and stirred for 30 min. The layers were separated and the organic layer was washed with water (3×50 mL) and 5% NaHCO3, dried, and concentrated to yield 2.0 g of crude product that was used without purification.
Workup
- temperatureThe resulting solution was cooled to rt
- concentrationconcentrated to minimum volume
- additionthen diluted with CHCl3 and ice
- customThe layers were separated
- washthe organic layer was washed with water (3×50 mL) and 5% NaHCO3
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-27d724ec5406428f8d7a9145ed265eeb
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686142B2
Reaction notes
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