Triethylamine → HCID 178437133, compound

HRID 630221Notes

Reaction equation

HRID 630221 reaction equation
Br.Br[CH2:3][C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1[CH2:11][CH3:12].[CH3:13][C:14]1[N:19]=[C:18]([SH:20])[N:17]=[C:16]([OH:21])[CH:15]=1.C(N(CC)CC)C>C(O)C>[CH2:11]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([F:10])[C:4]=1[CH2:3][S:20][C:18]1[N:17]=[C:16]([OH:21])[CH:15]=[C:14]([CH3:13])[N:19]=1)[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66815164HCID 66815164, compoundHCID 178429541HCID 178429541, compound

Product 1

HCID 178437133HCID 178437133, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)-3-ethyl-5-fluoropyridine hydrobromide (9.7 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (1.7 g, 12 mmol), and triethylamine (3.5 mL, 25 mmol) in absolute ethanol (100 mL) was stirred at overnight room temperature. The mixture was evaporated. Water (100 mL) and EtOAc (100 mL) were added. The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude mixture was purified by flash chromatography (0-5% MeOH/CH2Cl2), affording the title compound (250 mg, 9% yield); 1H NMR (500 MHz, DMSO-d6): δ 1.21 (t, 3H, J=7.5 Hz), 2.23 (s, 3H), 2.83 (q, 2H, J=7.5 Hz), 4.51 (s, 2H), 6.07 (s, 1H), 8.33 (s, 1H), 8.41 (s, 1H); M+280.

Workup

  1. customThe mixture was evaporated
  2. additionWater (100 mL) and EtOAc (100 mL) were added
  3. customThe organic layer was recovered
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo
  8. customThe crude mixture was purified by flash chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3492d4df939d412598ba2be26078c5c3
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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