Boron tribromide → (2-Anilino-6-methylpyrimidin-4-yl)methanol

HRID 981482Notes

Reaction equation

HRID 981482 reaction equation
B(Br)(Br)Br.[NH:5]([C:12]1[N:17]=[C:16]([CH2:18][O:19]C)[CH:15]=[C:14]([CH3:21])[N:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[NH:5]([C:12]1[N:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:14]([CH3:21])[N:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 143275464-(Methoxymethyl)-6-methyl-N-phenylpyrimidin-2-amine

Product 1

HCID 14327569(2-Anilino-6-methylpyrimidin-4-yl)methanolYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron bromide (3.9 g) was added dropwise to a solution of 3.0 g of 2-anilino-4-methoxymethyl-6-methylpyrimidine in 100 ml of dichloromethane at -70° C. After completion of the dropwise addition, the coolant was removed and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water gradually. The organic layer was washed with water, dried over magnesium sulfate and concentrated. The solid residue was recrystallized from ethanol-hexane to obtain 2.5 g (yield: 89%) of 2-anilino-4-hydroxymethyl-6-methyl-pyrimidine having a melting point of 118°-120° C.

Workup

  1. additionAfter completion of the dropwise addition
  2. customthe coolant was removed
  3. additionThe reaction mixture was poured into water gradually
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe solid residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-cab7d31ab71f4106b0a9d5b97c7ded55
Source dataset
uspto-grants-1991_02
Patent number
US04992438

Reaction notes

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