Ammonia → 6-(3-Chlorophenyl)-2-ethyl-4(3H)-pyrimidinone

HRID 1509001Notes

Reaction equation

HRID 1509001 reaction equation
[OH-].[NH4+:2].[NH3:3].C(O[C:7](OCC)(OCC)[CH2:8][CH3:9])C.[Cl:16][C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][C:25]([O:27]CC)=O)[CH:20]=[CH:21][CH:22]=1>CO.C(O)C>[Cl:16][C:17]1[CH:18]=[C:19]([C:23]2[N:3]=[C:7]([CH2:8][CH3:9])[NH:2][C:25](=[O:27])[CH:24]=2)[CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14923Ammonium Hydroxide2×HCID 66995Ethyl orthopropionateHCID 2757831Ethyl (3-chlorobenzoyl)acetate

Product 1

HCID 1365098196-(3-Chlorophenyl)-2-ethyl-4(3H)-pyrimidinoneYield 6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ammonium hydroxide (3 mL) and ammonia in methanol (7.0 N, 10 mL) in ethanol (6 mL) was added 1,1,1-triethoxypropane (6.2 g, 35.3 mmol) and ethyl 3-(3-chlorophenyl)-3-oxopropanoate (4.0 g, 17.6 mmol) dropwise as a solution in ethanol (10 mL). Once the addition was complete, ammonium hydroxide (10 mL) was added. The mixture was heated with stirring in a sealed flask at 60° C. overnight. After this time, the mixture was cooled to rt and concentrated. The residue was purified by column chromatography (silica, hexanes/DCM) to afford the title compound (0.250 g, 6%) as a white solid. MW=234.68. 1H NMR (CDCl3, 500 MHz) δ 8.03 (t, J=1.9 Hz, 1H), 7.86-7.82 (m, 1H), 7.46-7.38 (m, 2H), 6.73 (s, 1H), 2.80 (q, J=7.6 Hz, 2H), 1.42 (t, J=7.6 Hz, 3H); APCI MS m/z 235 [M+H]+.

Workup

  1. additionOnce the addition
  2. temperatureThe mixture was heated
  3. temperatureAfter this time, the mixture was cooled to rt
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, hexanes/DCM)

Sources & evidence

ORD record
ord-410785a3ece1443c8e9847aad99c2688
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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