Potassium Carbonate → HCID 59184680, compound

HRID 426152Notes

Reaction equation

HRID 426152 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[Li+].[Cl:30][C:31]1[N:36]=[C:35]([CH2:37]Cl)[CH:34]=[CH:33][N:32]=1>CN(C=O)C>[Cl:30][C:31]1[N:36]=[C:35]([CH2:37][N:12]2[C:7]([C:5](=[O:6])[C:4]3[CH:3]=[C:2]([CH3:1])[CH:20]=[C:19]([CH3:21])[CH:18]=3)=[C:8]([CH:15]([CH3:17])[CH3:16])[C:9](=[O:14])[NH:10][C:11]2=[O:13])[CH:34]=[CH:33][N:32]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 216981282-Chloro-4-(chloromethyl)pyrimidineHCID 222565826-(3,5-Dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione

Product 1

HCID 59184680HCID 59184680, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (20) (286 mg, 1 mmol), anhydrous powdered potassium carbonate (134 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 ml) at room temperature, was added 2-Chloro-4-chloromethyl-pyrimidine (164 mg, 1 mmol). After stirring for overnight, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1)) to afford 210 mg (51%) of a white solid. m.p. 197-198° C.; 1H NMR (300 MHz, CDCl3) δ 1.17 (3H, d, J=6.9 Hz), 1.21 (3H, d, J=6.9 Hz), 2.29-2.39 (7H, m), 4.73 (1H, d, J=17.4 Hz), 4.95 (1H, d, J=17.4 Hz), 7.07 (1H, d, J=5.1 Hz), 7.28 (1H, s), 7.48 (2H, s), 8.46 (1H, d, J=5.1 Hz), 9.41 (1H, s); m/z (EI) 412 (M+).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:1))

Sources & evidence

ORD record
ord-3b058a2a00b143eb9f587b90036abb05
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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