Triethylamine → HCID 178433538, compound

HRID 630297Notes

Reaction equation

HRID 630297 reaction equation
Br.Br[CH2:3][C:4]1[S:8][CH:7]=[N:6][C:5]=1[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>[CH3:9][C:5]1[N:6]=[CH:7][S:8][C:4]=1[CH2:3][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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668206655-(Bromomethyl)-4-methyl-1,3-thiazole hydrobromideHCID 178516148HCID 178516148, compound

Product 1

HCID 178433538HCID 178433538, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. mixture of 5-(bromomethyl)-4-methyl-1,3-thiazole hydrobromide (19.4 mmol) and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (2.47 g, 12.6 mmol) in absolute ethanol (100 mL) was added triethylamine (8.00 mL, 57.4 mmol). The mixture was stirred at room temperature for 2 days. The solid material was removed by filtration and washed with diethyl ether (100 mL). The filtrate was evaporated to dryness and then co-evaporated with ethyl acetate (1×50 mL). The solid residue was treated with water (100 mL), and the mixture was stirred for 30 minutes. The solid product was recovered by filtration, washed with water (2×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL), and then dried in vacuo to afford 2-{[(4-methyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (1.76 g, 45%); 1H NMR (500 MHz, DMSO-d6): δ 2.39 (s, 3H), 4.61 (s, 2H), 6.65 (s, 1H), 8.86 (s, 1H); M+308.

Workup

  1. customThe solid material was removed by filtration
  2. washwashed with diethyl ether (100 mL)
  3. customThe filtrate was evaporated to dryness
  4. additionThe solid residue was treated with water (100 mL)
  5. stirringthe mixture was stirred for 30 minutes
  6. filtrationThe solid product was recovered by filtration
  7. washwashed with water (2×25 mL), diethyl ether (2×25 mL), and hexanes (2×25 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-d5b932feff0342348c3fc032e719971b
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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