Triethylamine → HCID 178463926, compound

HRID 577014Notes

Reaction equation

HRID 577014 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5](CN(CC)CC)C=[CH:7][C:8]=1[Cl:9].[CH3:16][C:17]1[N:22]=[C:21]([SH:23])[N:20]=[C:19]([OH:24])[CH:18]=1.[CH2:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26]>C(O)C>[Cl:9][C:8]1[CH:7]=[C:26]([CH2:25][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH:5]=[CH:4][C:3]=1[CH2:2][S:23][C:21]1[N:20]=[C:19]([OH:24])[CH:18]=[C:17]([CH3:16])[N:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66815196Benzenemethanamine, 3-(bromomethyl)-4-chloro-N,N-diethyl-HCID 178429541HCID 178429541, compound

Product 1

HCID 178463926HCID 178463926, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of {[3-(bromomethyl)-4-chlorophenyl]methyl}diethylamine (13.2 mmol), 6-methyl-2-sulfanylpyrimidin-4-ol (1.07 g, 7.5 mmol), and triethylamine (8 mL, 57.4 mmol) in absolute ethanol (50 mL) was stirred at room temperature overnight. The mixture was evaporated and then co-evaporated with EtOAc (20 mL). The solid residue was treated with water (100 mL). The solution was extracted with dichloromethane (5×100 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-15% MeOH/CH2Cl2), affording the title compound (932 mg, 39% yield); 1H NMR (400 MHz, DMSO-d6): δ 1.11 (t, 6H, J=6.8 Hz), 2.21 (s, 3H), 2.86 (m, 4H), 4.09 (s (br), 2H), 4.45 (s, 2H), 6.01 (s (br), 1H), 7.45 (m, 1H), 7.52 (m, 1H), 7.72 (s, 1H); M+ 352.

Workup

  1. customThe mixture was evaporated
  2. additionThe solid residue was treated with water (100 mL)
  3. extractionThe solution was extracted with dichloromethane (5×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo
  8. customThe crude product was purified by flash chromatography (0-15% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-544bd2fe9f2a43709dbeb296888d5f39
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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