Sodium Carbonate → 5-Chloro-1-(2-triphenylmethylaminothiazol-4-ylmethyl)pyrimidin-2-one

HRID 434647

Reaction equation

HRID 434647 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Cl[CH2:10][C:11]1[N:12]=[C:13]([NH:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:14][CH:15]=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]([CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:14][CH:15]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1085785-Chloro-2(1H)-pyrimidinoneHCID 137451724-Chloromethyl-2-tritylaminothiazole

Product 1

HCID 204917735-Chloro-1-(2-triphenylmethylaminothiazol-4-ylmethyl)pyrimidin-2-oneYield 79.4%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of 5-chloropyrimidin-2-one (688 mg), 4-chloromethyl-2-triphenylmethylaminothiazole (3.000 g), anhydrous sodium carbonate (1.086 g) and benzyltrimethylammonium chloride (20 mg) in dry N,N-dimethylformamide (25 ml) was heated at 90° C. After 1.5 h the reaction mixture was evaporated to dryness. The residue was suspended in ethyl acetate (250 ml) and washed with water (2×60 ml) and brine (60 ml), then dried and evaporated to a dark brown foam. The foam was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 24:1. This gave a brown foam which was triturated with diethyl ether to give a brown solid (2.03 g). A portion of the solid (360 mg) was recrystallised from ethyl acetate to give buff crystals of the title pyrimidinone (129 mg), m.p. 215°-216° C., λmax (EtOH) 268 nm (ε 8,630), 335 nm (ε 3,440).

Workup

  1. customAfter 1.5 h the reaction mixture was evaporated to dryness
  2. washwashed with water (2×60 ml) and brine (60 ml)
  3. customdried
  4. customevaporated to a dark brown foam
  5. washeluting with chloroform-ethanol, 24:1
  6. customThis gave a brown foam which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-a2a003919abc43a1bab526a3d49447b9
Source dataset
uspto-grants-1983_08
Patent number
US04399140

Linked notes

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