Ammonia → 2-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetamide

HRID 1508935Notes

Reaction equation

HRID 1508935 reaction equation
[NH3:1].[CH:2]1([C:7]2[N:12]=[C:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=O)=[CH:16][CH:15]=3)[CH:10]=[C:9]([CH2:25][CH3:26])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1>>[CH:2]1([C:7]2[N:12]=[C:11]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][C:21]([NH2:1])=[O:23])=[CH:18][CH:19]=3)[CH:10]=[C:9]([CH2:25][CH3:26])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 90109465Methyl 2-(4-((2-cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetate

Product 1

HCID 901130332-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetamideYield 59%

Conditions

Temperature
100 °C

Procedure

A mixture of ammonia (7.0 N in methanol, 4 mL) and methyl 2-(4-((2-cyclopentyl-6-ethylpyrimidin-4-yl)methyl)phenyl)acetate (0.067 g, 0.20 mmol) and heated at 100° C. for 48 h. After this time, the mixture was cooled and filtered through celite with ethyl acetate washings. The filtrate was washed with brine (3×15 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.039 g, 59%) as a white solid. MW=323.43. 1H NMR (DMSO-d6, 500 MHz) δ 7.44 (s, 1H), 7.27-7.11 (m, 4H), 7.01 (s, 1H), 6.86 (s, 1H), 3.95 (s, 2H) 3.31 (s, 2H), 3.29-3.14 (m, 1H), 2.62 (q, J=7.6 Hz, 2H), 2.06-1.91 (m, 2H), 1.90-1.67 (m, 4H), 1.66-1.53 (m, 2H), 1.16 (t, J=7.6 Hz, 3H); APCI MS m/z 324 [M+H]+.

Workup

  1. temperatureAfter this time, the mixture was cooled
  2. filtrationfiltered through celite with ethyl acetate washings
  3. washThe filtrate was washed with brine (3×15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a00bfc8f12374c208724e43ed8801de7
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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