Triethylamine → HCID 49806011, compound

HRID 576916Notes

Reaction equation

HRID 576916 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[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([SH:20])[N:14]=1.C(N(CC)CC)C>C(O)C>[CH3:19][C:17]1[N:16]=[C:15]([S:20][CH2:2][C:3]2[C:4]([Cl:11])=[CH:5][CH:6]=[C:7]([Cl:10])[C:8]=2[Cl:9])[N:14]=[C:13]([NH2:12])[CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 786622-(Bromomethyl)-1,3,4-trichlorobenzeneHCID 178428717HCID 178428717, compound

Product 1

HCID 49806011HCID 49806011, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 mL round bottom flask, 2-(bromomethyl)-1,3,4-trichlorobenzene (550 mg, 2.0 mmol), 4-amino-6-methylpyrimidine-2-thiol (282 mg, 2.0 mmol), and triethylamine (0.28 mL, 2.0 mmol) were mixed in ethanol (10 mL). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated. To the crude solid, water (50 mL) was added. The suspension was filtered and washed with water and ethyl acetate to provide a white solid (530 mg, 95% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.18 (s, 3H), 4.65 (s, 2H), 6.03 (s, 1H), 6.90 (br, 1H), 7.55 (d, 1H), 7.64 (d, 1H); M+ 334, 336.

Workup

  1. customThe solvent was evaporated
  2. additionTo the crude solid, water (50 mL) was added
  3. filtrationThe suspension was filtered
  4. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-5b0b24dc7e134c7ca1630cca89429bd4
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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