Cesium carbonate → 2-Methylthio-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(3-(dimethylaminocarbonyl)-phenoxy)pyrimidine

HRID 1456951Notes

Reaction equation

HRID 1456951 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:15]=2)[N:4]=1.Cl.[CH2:26]([O:28][C:29](=[O:32])[CH2:30][NH2:31])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:31][CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:32])[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH:15]=2)[N:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 221026862-Methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine

Product 1

HCID 221033402-Methylthio-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(3-(dimethylaminocarbonyl)-phenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-methylthio-4-chloro-5-nitro-6-(3-(dimethylaminocarbonyl)phenoxy)pyrimidine, a compound of formula (C), (3.0 g 8.14 mmol) in 80 mL of acetonitrile at 0° C. was added glycine ethyl ester hydrochloride, a compound of formula (D), (1.14 g, 8.14 mmol), followed by the addition of cesium carbonate (6.1 g, 18.7 mmol). The reaction mixture was allowed to warm to ambient temperature and then stirred for 2 hours. The volatiles were evaporated to yield 3.6 g of 2-methylthio-4-(ethoxycarbonylmethyl)amino-5-nitro-6-(3-(dimethylaminocarbonyl)-phenoxy)pyrimidine, a compound of formula (E).

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-18290c507c3b461d9fb521c1822818fb
Source dataset
uspto-grants-1998_12
Patent number
US05846972

Reaction notes

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