Ethyl isothiocyanatoformate → HCID 58534942, compound

HRID 2197420Notes

Reaction equation

HRID 2197420 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([O:10][CH3:11])=[CH:5][N:4]=1.[CH3:12][CH2:13][O:14][C:15]([N:17]=[C:18]=[S:19])=[O:16]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][C:18]([NH:17][C:15](=[O:16])[O:14][CH2:13][CH3:12])=[S:19])[C:6]([O:10][CH3:11])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformate2×HCID 2503702,5-Dimethoxypyrimidin-4-amine

Product 1

HCID 58534942HCID 58534942, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

2,5-Dimethoxypyrimidin-4-amine (6) (3 g, 0.0193 moles) was dissolved in 18 g of ethyl acetate. Ethyl isothiocyanatidocarbonate (2.77 g, 0.0208 moles) was added in one portion. The solution was heated to 78° C. and held at that temperature for 11 h. An additional 1.4 g of the ethyl isothiocyanatidocarbonate was added and the mixture heated for 2.5 h. The mixture was allowed to cool to 22° C. and filtered. The resulting solid was washed with ethyl acetate (20 mL) and dried to a constant weight in a fume hood to afford the title compound as a yellow solid (4.81 g, 89%): 13C NMR (DMSO-d6, 100 MHz) δ 177.5, 158.4, 153.3, 149.5, 142.3, 139.5, 62.6, 57.6, 55.2, 14.4; HRMS (ESI), calcd for C10H14N4O4S, 286.0736; found, 286.0727.

Workup

  1. temperaturethe mixture heated for 2.5 h
  2. temperatureto cool to 22° C.
  3. filtrationfiltered
  4. washThe resulting solid was washed with ethyl acetate (20 mL)
  5. customdried to a constant weight in a fume hood

Sources & evidence

ORD record
ord-9e2eeaaf4e4642ab94f797c2aea690a2
Source dataset
uspto-grants-2012_12
Patent number
US08338596B2

Reaction notes

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