Potassium Carbonate → HCID 178429534, compound

HRID 630108Notes

Reaction equation

HRID 630108 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-f3a0d50cef38446aa15ad3b95412ef07
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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