Tert-Butyl nitrite → HCID 86749730, compound

HRID 1957178Notes

Reaction equation

HRID 1957178 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([N:19]([CH3:21])[CH3:20])[N:11]=[C:10]([CH3:22])[N:9]=1)([CH3:3])[CH3:2].C([O:30][N:31]=O)(C)(C)C>COCCOC>[CH:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[O:7][C:8]1[C:13]([C:14](=[N:31][OH:30])[C:15]([O:17][CH3:18])=[O:16])=[C:12]([N:19]([CH3:21])[CH3:20])[N:11]=[C:10]([CH3:22])[N:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 54378902HCID 54378902, compound

Product 1

HCID 86749730HCID 86749730, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-(3-isopropylphenoxy)-6-dimethylamino-2-methyl-pyrimidin-5-yl-acetate (28 g, 0.08 mol) in t-butylnitrite (40 ml) and 1,2-dimethoxyethane (40 ml) is added at -30° C. to a solution of potassium tert.butylate (14 g, 0.12 mol) in 1,2-dimethoxyethane (50 ml). The reaction mixture is allowed to warm to 0° C. and is the quenched with a solution of ammonium chloride. After stirring for 2 hours at room temperature the product is extracted with diethylether. Drying (MgSO4) and evaporation of the solvent gives crude methyl 2-[4-(3-isopropylphenoxy)-6-dimethylamino-2-methyl-pyrimidin-5-yl]-2-hydroximino-acetate (30 g).

Workup

  1. customquenched with a solution of ammonium chloride
  2. extractionis extracted with diethylether
  3. customDrying
  4. custom(MgSO4) and evaporation of the solvent

Sources & evidence

ORD record
ord-d6b794e7c58d42569fbb94c8be710d0f
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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