Ethyl Glycolate → HCID 22102969, compound

HRID 1456944Notes

Reaction equation

HRID 1456944 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[CH3:10][S:11][C:12]1[N:17]=[C:16](Cl)[C:15]([N+:19]([O-:21])=[O:20])=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH:24]=2)[N:13]=1>O1CCCC1>[CH3:10][S:11][C:12]1[N:17]=[C:16]([O:5][CH2:4][C:3]([O:7][CH2:8][CH3:9])=[O:6])[C:15]([N+:19]([O-:21])=[O:20])=[C:14]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([N:31]([CH3:32])[CH3:33])=[O:30])[CH:24]=2)[N:13]=1

Participants

5

Reactant 3

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 221026862-Methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine

Product 1

HCID 22102969HCID 22102969, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium hydride (0.63 g, 15.72 mmol) in 30 mL tetrahydrofuran at 0° C. was added ethyl glycolate (1.15 mL, 12.09 mmol) over 10 minutes. The resulting alkoxide was then added to 2-methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine, a compound of formula (C), (4.46 g., 12.09 mmol), dropwise at 0° C. over 5 minutes. After 1 hours, the reaction mixture was warmed to ambient temperature and stirred for an additional 2 hours. The volatiles were evaporated to yield 2.55 g (48% yield) of 2-methylthio-4-(ethoxycarbonyl)methoxy-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine, a compound of formula (Q), as a yellow oil.

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-79744269e1604264908d9135dc595548
Source dataset
uspto-grants-1998_12
Patent number
US05846970

Reaction notes

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