Potassium Carbonate → HCID 178429534, compound

HRID 577066Notes

Reaction equation

HRID 577066 reaction equation
Cl[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[CH3:8].[CH3:9][C:10]1[N:15]=[C:14]([SH:16])[N:13]=[C:12]([OH:17])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:9][C:10]1[N:15]=[C:14]([S:16][CH2:2][C:3]2[S:7][CH:6]=[N:5][C:4]=2[CH3:8])[N:13]=[C:12]([OH:17])[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2029845-(chloromethyl)-4-methyl-1,3-thiazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429534HCID 178429534, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5-(chloromethyl)-4-methyl-1,3-thiazole (887 mg, 4.9 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (600 mg, 4.2 mmol), and potassium carbonate (2.1 g, 15 mmol) in acetone (30 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was recovered and evaporated, co-evaporated with EtOAc (20 mL) and dried in vacuo. The solid residue was treated with diethyl ether (30 mL). The solid product was recovered by filtration, washed with diethyl ether (2×15 mL) and hexanes (1×15 mL), and dried in vacuo, affording 6-methyl-2-{[(4-methyl-1,3-thiazol-5-yl)methyl]sulfanyl}pyrimidin-4-ol (1.0 g, 93% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.91 (s, 3H), 2.34 (s, 3H), 4.31 (s, 2H), 5.32 (s, 1H), 8.73 (s, 1H); M+ 254. The product was used without further purification.

Workup

  1. customThe solid material was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated
  4. customdried in vacuo
  5. additionThe solid residue was treated with diethyl ether (30 mL)
  6. filtrationThe solid product was recovered by filtration
  7. washwashed with diethyl ether (2×15 mL) and hexanes (1×15 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f767a807db0444528045d963e1ace862
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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