Ammonium Chloride → HCID 22599869, compound

HRID 1592188Notes

Reaction equation

HRID 1592188 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:2]#[C:3][CH3:4].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([CH:12]([OH:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 22599721HCID 22599721, compound

Product 1

HCID 22599869HCID 22599869, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

In 2 ml of ethanol was suspended 0.5 g of 6-(2-butynyloxy)-4-benzoylpyrimidine, to which 0.11 g of sodium borohydride was added, followed by stirring at 0° C. for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was then dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 0.4 g of 6-(2-butynyloxy)-4-(α-hydroxybenzyl)pyrimidine (the present compound (123)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialthe combined organic layer was then dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89d41f09424e45eab2a6c7f3424b5b6c
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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