Sodium Carbonate → HCID 20491762, compound

HRID 434644Notes

Reaction equation

HRID 434644 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[S:9]([C:13]1[CH:19]=[CH:18][C:16](C)=[CH:15][CH:14]=1)(O)(=O)=O.OCCC1SC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:19][CH2:18][C:16]2[S:9][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 85813337HCID 85813337, compound

Product 1

HCID 20491762HCID 20491762, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of 5-chloropyrimidin-2-one (131 mg), 2-(2-hydroxyethyl)thiophene tosylate (424 mg), anhydrous sodium carbonate (265 mg) and benzyltrimethylammonium chloride (4 mg) in dry N,N-dimethylformamide (5 ml) was heated at 90° C. After 41/2 h the reaction mixture was evaporated to dryness and the residue was suspended in ethyl acetate (50 ml) and washed with water (3×15 ml), dried (MgSO4) and evaporated to a solid. The solid was subjected to p.l.c. on silica developing with chloroform-ethanol, 19:1. The more polar band was eluted with ethyl acetate and crystallised twice from acetone to give white crystals of the title pyrimidinone (94 mg), m.p. 182°-183° C., λmax (EtOH) 230 nm (ε 17,190), 335 nm (ε 3,470).

Workup

  1. customAfter 41/2 h the reaction mixture was evaporated to dryness
  2. washwashed with water (3×15 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a solid
  5. washThe more polar band was eluted with ethyl acetate
  6. customcrystallised twice from acetone

Sources & evidence

ORD record
ord-dabccb9155ab4c5ca96a08ebb5f9df74
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Reaction notes

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