Triethylamine → HCID 178429441, compound

HRID 630027Notes

Reaction equation

HRID 630027 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([Cl:8])[S:5][C:4]=1[Cl:9].[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>[Cl:9][C:4]1[S:5][C:6]([Cl:8])=[CH:7][C:3]=1[CH2:2][S:17][C:15]1[N:14]=[C:13]([OH:18])[CH:12]=[C:11]([CH3:10])[N:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 234340823-(Bromomethyl)-2,5-dichlorothiopheneHCID 178429541HCID 178429541, compound

Product 1

HCID 178429441HCID 178429441, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(bromomethyl)-2,5-dichlorothiophene (125 mg, 0.51 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (60 mg, 0.42 mmol), and triethylamine (180 μL, 1.3 mmol) in absolute ethanol (5 mL) was stirred at room temperature overnight. The mixture was recovered and evaporated. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (1×15 mL), diethyl ether (2×15 mL), and hexanes (2×15 mL), and then dried in vacuo, affording 2-{[(2,5-dichlorothiophen-3-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol (91 mg, 71% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.27 (s, 2H), 6.02 (s (br), 1H), 7.17 (s 1H); M+308.

Workup

  1. customThe mixture was recovered
  2. customevaporated
  3. additionThe solid residue was treated with water (100 mL)
  4. filtrationThe solid product was recovered by filtration
  5. washwashed with water (1×15 mL), diethyl ether (2×15 mL), and hexanes (2×15 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d0e6285521984dad8dbf06378c77d60a
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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