Triethylamine → HCID 178507959, compound

HRID 576917Notes

Reaction equation

HRID 576917 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([Cl:10])[CH:6]=[CH:5][C:4]=1[Cl:11].[NH2:12][C:13]1[N:18]=[C:17]([SH:19])[N:16]=[C:15]([OH:20])[CH:14]=1.C(N(CC)CC)C>C(O)C>[NH2:12][C:13]1[N:18]=[C:17]([S:19][CH2:2][C:3]2[C:4]([Cl:11])=[CH:5][CH:6]=[C:7]([Cl:10])[C:8]=2[Cl:9])[N:16]=[C:15]([OH:20])[CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 786622-(Bromomethyl)-1,3,4-trichlorobenzeneHCID 178507961HCID 178507961, compound

Product 1

HCID 178507959HCID 178507959, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bromomethyl)-1,3,4-trichlorobenzene (580 mg, 2.1 mmol), 6-amino-2-sulfanylpyrimidin-4-ol (290 mg, 1.8 mmol), and triethylamine (280 μL, 2.0 mmol) in absolute ethanol (10 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure. The solid product was suspended in water (50 mL). The solid material was recovered by filtration, washed with water (1×20 mL) and diethyl ether (2×20 mL), and dried in vacuo, affording the title compound (325 mg, 54% yield); 1H NMR (400 MHz, DMSO-d6): δ 4.64 (s, 2H), 5.03 (s, 1H), 6.57 (s (br), 2H), 7.54 (d, 1H, J=8.8 Hz), 7.64 (d, 1H, J=8.8 Hz); M+ 337; HPLC purity: 95.5%.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe solid material was recovered by filtration
  3. washwashed with water (1×20 mL) and diethyl ether (2×20 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d516a29747e84fc1943af0c7572b9388
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

Loading…