Triethylamine → HCID 178429531, compound

HRID 630047Notes

Reaction equation

HRID 630047 reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][C:4]=1[Cl:9].[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[Cl:8][C:6]1[S:7][C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[C:4]([Cl:9])[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 223492195-(Bromomethyl)-2,4-dichloro-1,3-thiazoleHCID 178429541HCID 178429541, compound

Product 1

HCID 178429531HCID 178429531, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-2,4-dichloro-1,3-thiazole, 6-methyl-2-sulfanylpyrimidin-4-ol (500 mg, 3.5 mmol), and triethylamine (2.5 mL, 18.0 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The solid material was removed by filtration. The filtrate was evaporated and then co-evaporated with EtOAc (20 mL). The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL), and then dried in vacuo. The crude product was purified by flash chromatography (0-5% MeOH/CH2Cl2), affording the title compound (778 mg, 72% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.27 (s, 3H), 4.46 (s, 2H), 6.09 (s (br), 1H); M+310.

Workup

  1. customThe solid material was removed by filtration
  2. customThe filtrate was evaporated
  3. additionThe solid residue was treated with water (100 mL)
  4. filtrationThe solid product was recovered by filtration
  5. washwashed with water (2×20 mL), diethyl ether (2×20 mL), and hexanes (2×20 mL)
  6. customdried in vacuo
  7. customThe crude product was purified by flash chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f45f1e1634494347b53b9e6f233492b9
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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