Ammonium Chloride → HCID 22599869, compound

HRID 1759910Notes

Reaction equation

HRID 1759910 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-c2977a96156e43c5a06c9cc269cc1e30
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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