Cesium carbonate → HCID 52417091, compound

HRID 1938179Notes

Reaction equation

HRID 1938179 reaction equation
CS[C:3]1N=C(Cl)C([N+]([O-])=O)=[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.C(O[C:29](=O)[CH2:30][NH2:31])C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:24][N:22]([CH3:23])[C:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][C:5]1[N:4]=[CH:3][CH:29]=[CH:30][N:31]=1)=[O:21]

Participants

5

Reactant 3

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

Product 1

HCID 52417091HCID 52417091, compound

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)-phenoxypyrimidine, a compound of formula (E).

Workup

  1. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-f1f77955c23a47d59fbb7c4c75d1b4da
Source dataset
uspto-grants-1997_12
Patent number
US05693641

Reaction notes

Loading…