Triethylamine → HCID 178429483, compound

HRID 629964Notes

Reaction equation

HRID 629964 reaction equation
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1.[CH3:8][C:9]1[N:14]=[C:13]([SH:15])[N:12]=[C:11]([OH:16])[CH:10]=1.C(N(CC)CC)C>C(O)C>[CH3:8][C:9]1[N:14]=[C:13]([S:15][CH2:2][C:3]2[CH:7]=[CH:6][S:5][CH:4]=2)[N:12]=[C:11]([OH:16])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5207033-(Bromomethyl)thiopheneHCID 178429541HCID 178429541, compound

Product 1

HCID 178429483HCID 178429483, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(bromomethyl)thiophene (360 mg, 2.0 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (242 mg, 1.7 mmol), and triethylamine (280 μL, 2.0 mmol) in absolute ethanol (10 mL) was stirred at room temperature for 2 days. The solid residue was removed by filtration. The filtrate was recovered and evaporated under reduced pressure. The solid product was suspended in water (20 mL). The solid material was recovered by filtration, washed with water (2×15 mL) and hexanes (3×15 mL), and dried in vacuo, affording the title compound (80 mg, 20% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.39 (s, 2H), 6.02 (s (br), 1H), 7.12 (dd, 1H, J=1.3 Hz, 3.5 Hz), 7.47 (m, 2H); M+239; HPLC purity: 96.1%.

Workup

  1. customThe solid residue was removed by filtration
  2. customThe filtrate was recovered
  3. customevaporated under reduced pressure
  4. filtrationThe solid material was recovered by filtration
  5. washwashed with water (2×15 mL) and hexanes (3×15 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f8fda3b615ad4f9ab526445fab5aa525
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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