Triethylamine → HCID 178429445, compound

HRID 630017Notes

Reaction equation

HRID 630017 reaction equation
Br[CH2:2][C:3]1[C:4]([F:9])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11]1[N:16]=[C:15]([SH:17])[N:14]=[C:13]([OH:18])[CH:12]=1.C(N(CC)CC)C>C(O)C>[F:9][C:4]1[C:3]([CH2:2][S:17][C:15]2[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=2)=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 230708853-(Bromomethyl)-2-fluoropyridineHCID 178429541HCID 178429541, compound

Product 1

HCID 178429445HCID 178429445, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(bromomethyl)-2-fluoropyridine, 6-methyl-2-sulfanylpyrimidin-4-ol (1.42 g, 10 mmol) and triethylamine (1.54 mL, 11 mmol) were mixed in ethanol (50 mL). The mixture was stirred at room temperature for 2 hours. After evaporation, water (100 mL) was added. The suspension was filtered and washed with water and ethyl acetate to provide pure titled product (1.8 g, 72% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.17 (s, 3H), 4.35 (s, 2H), 6.00 (br, 1H), 7.28 (m, 1H), 8.05 (m, 1H), 8.11 (m, 1H); M+252.

Workup

  1. customAfter evaporation, water (100 mL)
  2. additionwas added
  3. filtrationThe suspension was filtered
  4. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-f68436fefeb24dff8b25bb08ee379672
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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