Triethylamine → HCID 178429533, compound

HRID 577065Notes

Reaction equation

HRID 577065 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[Cl:8].[CH3:9][C:10]1[N:15]=[C:14]([SH:16])[N:13]=[C:12]([OH:17])[CH:11]=1.C(N(CC)CC)C>C(O)C>[Cl:8][C:4]1[N:5]=[CH:6][S:7][C:3]=1[CH2:2][S:16][C:14]1[N:13]=[C:12]([OH:17])[CH:11]=[C:10]([CH3:9])[N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59589444HCID 59589444, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178429533HCID 178429533, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-4-chloro-1,3-thiazole (8.4 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (850 mg, 6.0 mmol), and triethylamine (3.5 mL, 25 mmol) in absolute ethanol (45 mL) was stirred at room temperature overnight. The mixture was evaporated to dryness and then co-evaporated with EtOAc (20 mL). The residue was treated with water (100 mL). The solid material was recovered by filtration and washed with water (3×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL). The solid material was dried in vacuo. The crude product was purified by flash chromatography (0-4% MeOH/DCM), affording the title compound (491 mg, 31% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 4.62 (s, 2H), 6.05 (s, 1H), 8.82 (s, 1H); M+ 274.

Workup

  1. customThe mixture was evaporated to dryness
  2. additionThe residue was treated with water (100 mL)
  3. filtrationThe solid material was recovered by filtration
  4. washwashed with water (3×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL)
  5. customThe solid material was dried in vacuo
  6. customThe crude product was purified by flash chromatography (0-4% MeOH/DCM)

Sources & evidence

ORD record
ord-8203658aed12478db95dfae7f57022b6
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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