Diethyl Ether → 2-[(2-ethyl-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 577173Notes

Reaction equation

HRID 577173 reaction equation
Br[CH2:2][C:3]1[C:4]([CH2:9][CH3:10])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]1[N:17]=[C:16]([SH:18])[N:15]=[C:14]([OH:19])[CH:13]=1.C(N(CC)CC)C.C(OCC)C>C(O)C>[CH2:9]([C:4]1[C:3]([CH2:2][S:18][C:16]2[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=2)=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 595894103-(Bromomethyl)-2-ethylpyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 1784375952-[(2-ethyl-3-pyridinyl)methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 0° C. mixture of 3-(bromomethyl)-2-ethylpyridine (21.9 mmol) and 6-methyl-2-sulfanylpyrimidin-4-ol (2.0 g, 14 mmol) in absolute ethanol (200 mL) was added triethylamine (11 mL, 79 mmol). The mixture was stirred at room temperature overnight. Diethyl ether (300 mL) was added to the clear solution. The precipitate was removed by filtration. The filtrate was recovered, evaporated, and co-evaporated with EtOAc (1×100 mL). The residue was treated with water (300 mL). The solid material was recovered by filtration, washed with water (3×50 mL), diethyl ether (2×50 mL), and hexanes (1×50 mL), and dried in vacuo, affording 2-{[(2-ethylpyridin-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (1.9 g, 52% yield), which was used without further purification.

Workup

  1. customThe precipitate was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated
  4. additionThe residue was treated with water (300 mL)
  5. filtrationThe solid material was recovered by filtration
  6. washwashed with water (3×50 mL), diethyl ether (2×50 mL), and hexanes (1×50 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-e8507dfc824348a39f345cc866f1e1f2
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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