Boron tribromide → HCID 68669560, compound

HRID 2071048Notes

Reaction equation

HRID 2071048 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH2:10][O:11]C)[N:7]=[C:6]([NH2:13])[N:5]=1)([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[NH2:13][C:6]1[N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68671207HCID 68671207, compound

Product 1

HCID 68669560HCID 68669560, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-isopropyl-6-(methoxymethyl)pyrimidin-2-amine (537 mg, 3.0 mmol) in CH2Cl2 (30 mL) at 0° C. was added BBr3 (3 mL of 1.0 M solution, 3 mmol) dropwise. The reaction was quenched with saturated aqueous NaHCO3 after 4 h. The resulting mixture was extracted with CH2Cl2 (2×20 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide (2-amino-6-isopropylpyrimidin-4-yl)methanol as a dark brown oil which was used for next step without further purification. 1H NMR (CDCl3): d 6.49 (s, 1H), 5.06 (br, 2H), 4.59 (s, 2H), 2.78-2.87 (m, 1H), 1.25 (m, 6H).

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 after 4 h
  2. extractionThe resulting mixture was extracted with CH2Cl2 (2×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa150b091b634ab7b6191ff45a850fd0
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…