Potassium Carbonate → HCID 58837304, compound

HRID 2356348Notes

Reaction equation

HRID 2356348 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:6]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[N:5][C:4]=1[S:25][CH3:26])#[N:2].C(=O)([O-])[O-:28].[K+].[K+]>C(O)C>[C:1](/[C:3](/[C:8]([NH:7][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:9])=[C:4](/[NH:5][C:6](=[O:28])[C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=1)\[S:25][CH3:26])#[N:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 9842817HCID 9842817, compound

Product 1

HCID 58837304HCID 58837304, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-Cyano-1-(4-methylphenyl)-4-(methylthio)-2-[4-(methylthio)phenyl]-6-oxo-1,6-dihydropyrimidine (2.5 g, 6.59 mmol) in ethanol (30 ml) was added anhydrous potassium carbonate (1.3 g, 9.4 mmol) under continuos stirring, and at an ambient temperature. The suspension was heated slowly to 60° C. under stirring for 5 hours. Subsequently the reaction mixture was filtered, and washed with water then with ethanol and dried under vacuum to yield the title compound (2.12 g, 80.8%, m.p.: 173-175° C., purity 91.6% by HPLC). 1H-NMR (CDCl3)δ (ppm): 2.34 (s, 3H), 2.53 (s, 3H), 2.69 (s, 3H), 7.16-7.18 (d, 2H), 7.26-7.37 (m, 4H), 7.92-7.94 (d, 2H), 14.0 (s, 1H, D2O exchangeable). IR (KBr) cm−1: 3311, 2201, 1702 (—C═O). MS m/z: 398.5 (M++1).

Workup

  1. customat an ambient temperature
  2. stirringunder stirring for 5 hours
  3. filtrationSubsequently the reaction mixture was filtered
  4. washwashed with water
  5. dry with materialwith ethanol and dried under vacuum

Sources & evidence

ORD record
ord-62c5dcf64a65474b8bcebd647ad30bc2
Source dataset
uspto-grants-2010_07
Patent number
US07759350B2

Reaction notes

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