Triethylamine → 2-[[2-chloro-6-(diethylaminomethyl)phenyl]methylsulfanyl]-6-methyl-1H-pyrimidin-4-one

HRID 577218Notes

Reaction equation

HRID 577218 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13].[CH3:16][C:17]1[N:22]=[C:21]([SH:23])[N:20]=[C:19]([OH:24])[CH:18]=1.C(N(CC)CC)C>C(O)C>[Cl:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[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 59589422{[2-(Bromomethyl)-3-chlorophenyl]methyl}diethylamineHCID 178429541HCID 178429541, compound

Product 1

HCID 1784639192-[[2-chloro-6-(diethylaminomethyl)phenyl]methylsulfanyl]-6-methyl-1H-pyrimidin-4-oneYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of {[2-(bromomethyl)-3-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), and 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 2-[({2-chloro-6-[(diethylamino)methyl]phenyl}methyl)sulfanyl]-6-methylpyrimidin-4-ol (932 mg, 39% yield); 1H NMR (400 MHz, DMSO-d6): δ 0.96 (t, 6H, J=6.8 Hz), 2.21 (s, 3H), 2.86 (m, 4H), 4.69 (s, 2H), 6.01 (s 1H), 7.35 (m, 1H), 7.42 (m, 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-ac1f407727b5419986818f41cec3db46
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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