Ethyl Acetate → 6-(4-Bromo-2-chlorophenyl)-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one

HRID 387224Notes

Reaction equation

HRID 387224 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24]CC)=O)=[C:17]([Cl:27])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CC(N(C)C)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22](=[O:24])[N:3]([CH2:1][CH3:2])[C:4]3[N:5]=[C:6]([S:12][CH3:13])[N:7]=[CH:8][C:9]=3[CH:10]=2)=[C:17]([Cl:27])[CH:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehydeHCID 67119604Ethyl 2-(4-Bromo-2-chlorophenyl)acetate

Product 1

HCID 671196406-(4-Bromo-2-chlorophenyl)-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-oneYield 14.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-ethylamino-2-(methylthio)pyrimidine-5-carbaldehyde (9, 1.00 g, 5.07 mmol) in anhydrous dimethylacetamide (10 mL) was added ethyl 4-bromo-2-chlorophenylacetate (1.70 g, 6.12 mmol) and cesium carbonate (3.30 g, 10.13 mmol). The reaction mixture was stirred at 100° C. for 2 h. The mixture was poured into ice water and the orange solid was collected, washed with water, dried and purified by Teledyne-Isco using a hexane:ethyl acetate gradient (1:0→4:1) to afford the title compound as a white solid (0.30 g, 0.73 mmol, 14%). ESMS m/z 410 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.65 (s, 1H), 7.66 (d, J=1.5 Hz, 1H), 7.63 (s, 1H), 7.47 (dd, J=8.3, 1.5 Hz, 1H), 7.26 (d, J=8.3 Hz, 1H), 4.55 (q, J=7.0 Hz, 2H), 2.66 (s, 3H), 1.37 (t, J=7.0 Hz, 3H).

Workup

  1. customthe orange solid was collected
  2. washwashed with water
  3. customdried
  4. custompurified by Teledyne-Isco

Sources & evidence

ORD record
ord-420d0e1511dd40758bcf1cbe561cc718
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

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