Triethylamine → HCID 178437804, compound

HRID 630276Notes

Reaction equation

HRID 630276 reaction equation
Br[CH2:2][C:3]1[S:7][CH:6]=[N:5][C:4]=1[CH2:8][CH3:9].[SH:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([C:18]([F:21])([F:20])[F:19])[N:12]=1.C(N(CC)CC)C>C(O)C>[CH2:8]([C:4]1[N:5]=[CH:6][S:7][C:3]=1[CH2:2][S:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[C:13]([C:18]([F:21])([F:19])[F:20])[N:12]=1)[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595893325-(Bromomethyl)-4-ethyl-1,3-thiazoleHCID 178516148HCID 178516148, compound

Product 1

HCID 178437804HCID 178437804, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(bromomethyl)-4-ethyl-1,3-thiazole (5.2 mmol), 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (700 mg, 3.6 mmol), and triethylamine (1.5 mL, 11 mmol) in absolute ethanol (40 mL) was stirred at room temperature overnight. The mixture was evaporated. The residue was treated with diethyl ether (100 mL). The solid material was removed by filtration. The filtrate was recovered and evaporated. The crude product was purified by flash chromatography (0-4% MeOH/CH2Cl2), affording the title compound (900 mg, 78% yield); 1H NMR (500 MHz, DMSO-d6): δ 1.19 (t, 2H, J=7.5 Hz), 2.76 (m, 2H, J=7.5 Hz), 4.65 (s, 2H), 6.65 (s, 1H), 8.88 (s, 1H); M+322.

Workup

  1. customThe mixture was evaporated
  2. additionThe residue was treated with diethyl ether (100 mL)
  3. customThe solid material was removed by filtration
  4. customThe filtrate was recovered
  5. customevaporated
  6. customThe crude product was purified by flash chromatography (0-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c32255e52fc145338fa6a10dfb420209
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…