Triethylamine → HCID 178516147, compound

HRID 577255Notes

Reaction equation

HRID 577255 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[Cl:10].[SH:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[CH2:3][S:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668153214-(Bromomethyl)-3-chloropyridine hydrobromideHCID 178516148HCID 178516148, compound

Product 1

HCID 178516147HCID 178516147, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. mixture of 4-(bromomethyl)-3-chloropyridine hydrobromide (7.2 mmol) and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (922 mg, 4.7 mmol) in absolute ethanol (40 mL) was added triethylamine (4.0 mL, 28.7 mmol). The mixture was stirred at room temperature overnight. The solid material was removed by filtration. Diethyl ether (2×50 mL) was used to wash the recovered solid. The solid material was removed by filtration. The filtrate was evaporated to dryness and then co-evaporated with ethyl acetate (1×25 mL). The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2×30 mL), diethyl ether (1×30 mL), and hexanes (2×30 mL), and was dried in vacuo to afford 2-{[(3-chloropyridin-4-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (822 mg, 54%); 1H NMR (500 MHz, DMSO-d6): δ 4.50 (s, 2H), 6.66 (s, 1H), 7.58 (d, 1H, J=4.9 Hz), 8.47 (d, 1H, J=4.9 Hz), 8.64 (s, 1H); M+ 322.

Workup

  1. customThe solid material was removed by filtration
  2. washto wash the recovered solid
  3. customThe solid material was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. additionThe solid residue was treated with water (100 mL)
  6. filtrationThe solid product was recovered by filtration
  7. washwashed with water (2×30 mL), diethyl ether (1×30 mL), and hexanes (2×30 mL)
  8. customwas dried in vacuo

Sources & evidence

ORD record
ord-654216eb63b34aeba5903561a74e99bd
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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