Triethylamine → HCID 178429427, compound

HRID 576999Notes

Reaction equation

HRID 576999 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9]Br)[CH:3]=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(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][S:18][C:16]2[N:15]=[C:14]([OH:19])[CH:13]=[C:12]([CH3:11])[N:17]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneHCID 178429541HCID 178429541, compound

Product 1

HCID 178429427HCID 178429427, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-bromo-2-(bromomethyl)-1-chlorobenzene (4.76 g. 16.7 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (1.83 g, 12.9 mmol), and triethylamine (5 mL, 36.0 mmol) in absolute ethanol (200 mL) was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. The solid residue was treated with water (500 mL). The solid product was recovered by filtration, washed with water (2×50 mL), diethyl ether (3×50 mL), and hexanes (3×50 mL), and then dried in vacuo, affording the title compound (3.23 g, 56% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.39 (s, 2H), 6.00 (s (br), 1H), 7.41 (d, 1H, J=8.4 Hz), 7.53 (dd, 1H, J=2.3 Hz, 8.4 Hz), 7.86 (d, 1H, J=2.0 Hz); M+ 347.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionThe solid residue was treated with water (500 mL)
  3. filtrationThe solid product was recovered by filtration
  4. washwashed with water (2×50 mL), diethyl ether (3×50 mL), and hexanes (3×50 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-070ba8e15b8b403390a5ea667bc2d95f
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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