4-Methoxybenzyl alcohol → HCID 90102822, compound

HRID 1052559Notes

Reaction equation

HRID 1052559 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:18][C:19]1[C:24]([C:25](Cl)=[O:26])=[C:23]([Cl:28])[N:22]=[CH:21][N:20]=1>O1CCCC1.ClCCl>[Cl:18][C:19]1[C:24]([C:25]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:26])=[C:23]([Cl:28])[N:22]=[CH:21][N:20]=1

Participants

6

Reactant 3

HCID 77384-Methoxybenzyl alcoholHCID 8471TriethylamineHCID 121633604,6-Dichloro-pyrimidine-5-carbonyl chloride

Product 1

HCID 90102822HCID 90102822, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

(4-Methoxyphenyl)methanol (356 mg, 2.58 mmol) was dissolved in tetrahydrofuran (10 ml) and triethylamine (790 μl, 5.67 mmol) was added. Then a solution of 4,6-dichloropyrimidine-5-carbonyl chloride (600 mg, 2.84 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) in tetrahydrofuran (4 ml) was dropwise added. The reaction mixture was stirred at room temperature for 3 days. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated to give 732 mg (81% yield) of the title compound, that was used in the next step without further purification. Purity 84%.

Workup

  1. washwashed with 4% sodium bicarbonate solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-10a660aa72ef44c69c179e23ba2d77ce
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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