Tetrahydrofuran → HCID 12040176, compound

HRID 989603Notes

Reaction equation

HRID 989603 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:13]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][CH3:22])[C:14]=2[NH2:15])=[O:12])[N:4]=1.O1CCCC1.B.[Na]>O>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([CH:11]([OH:12])[C:13]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][CH3:22])[C:14]=2[NH2:15])[N:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 12979367HCID 12979367, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 12040176HCID 12040176, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.1 g (10 mM) of the 2-(4,6-dimethoxypyrimidine-2-ylcarbonyl)-6-methoxymethylaniline obtained in the above (4) was dissolved in 50 ml of a 1:1 (by volume ratio) mixed solvent of tetrahydrofuran and water. While the solution was stirred at room temperature, thereto was added 0.6 g (16 mM) of sodium boron hydride. The mixture was stirred at room temperature for 2 hours. 50 ml of ice water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and subjected to vacuum distillation to remove the solvent. The residual crystals were washed with diisopropyl ether to obtain 2.8 g (yield: 92%) of 2-[(4,6-dimethoxypyrimidine-2-yl)hydroxymethyl]-6-methoxymethylaniline as a white powder (melting point: 40 to 42° C.).

Workup

  1. dissolutionwas dissolved in 50 ml of a 1:1 (by volume ratio)
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. distillationsubjected to vacuum distillation
  7. customto remove the solvent
  8. washThe residual crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-fc0624bd66984cb1ad9787cea4eba683
Source dataset
uspto-grants-2002_10
Patent number
US06458748B1

Reaction notes

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