2-cyclopentyl-6-ethylpyrimidin-4(3H)-one → 4-Chloro-2-cyclopentyl-6-ethylpyrimidine

HRID 1508929Notes

Reaction equation

HRID 1508929 reaction equation
O(Cl)[Cl:2].[P+5].[CH:5]1([C:10]2[NH:15][C:14](=O)[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>[OH-].[Na+]>[Cl:2][C:14]1[CH:13]=[C:12]([CH2:17][CH3:18])[N:11]=[C:10]([CH:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)[N:15]=1

Participants

4

Reactant 2

HCID 1360851072-cyclopentyl-6-ethylpyrimidin-4(3H)-oneHCID 178479711HCID 178479711, compound

Product 1

HCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidineYield 57%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus(V) oxychloride (150 g, 99.0 mmol) was slowly added to 2-cyclopentyl-6-ethylpyrimidin-4(3H)-one (18.9 g, 98.3 mmol) at 0° C. Then, the reaction mixture was warmed to 100° C. for 3 h. After this time, the mixture was cooled, diluted with sodium hydroxide, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/dichloromethane) to afford the title compound (5.1 g, 57%) as yellow oil. MW=210.70. 1H NMR (CDCl3, 300 MHz) δ 7.01 (s, 1H), 3.36-3.20 (m, 1H), 2.74 (q, J=7.5 Hz, 2H), 2.14-1.99 (m, 2H), 1.98-1.76 (m, 4H), 1.75-1.63 (m, 2H), 1.29 (t, J=7.5 Hz, 3H); APCI MS m/z 211 [M+H]+.

Workup

  1. temperatureAfter this time, the mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, hexanes/dichloromethane)

Sources & evidence

ORD record
ord-252381d0f4b64e1d8bdcf79e55672179
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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