Ethyl isothiocyanatoformate → HCID 57476594, compound

HRID 250111

Reaction equation

HRID 250111 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[C:11]([N:16]=[C:17]=[S:18])(=[O:15])[O:12][CH2:13][CH3:14]>C1(C)C=CC=CC=1>[Cl:9][C:6]1[C:7]2[N:8]=[C:17]([NH:16][C:11](=[O:15])[O:12][CH2:13][CH3:14])[S:18][C:2]=2[N:3]=[C:4]([CH3:10])[N:5]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Product 1

HCID 57476594HCID 57476594, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 4,6-dichloro-2-methylpyrimidin-5-amine (1 g, 5.62 mmol) and O-ethyl carbonisothiocyanatidate (0.66 mL, 5.62 mmol) was added toluene (2 mL) to wet the solids completely. The mixture was placed on 100° C. oil bath for 1.5 hours, at which time, the mixture had seized to give a solid mass. The solids were cooled to ambient temperature and triturated with ether, then the resulting solids were collected by filtration to give ethyl 7-chloro-5-methylthiazolo[5,4-d]pyrimidin-2-ylcarbamate (1.08 g, 3.96 mmol, 70.5% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.70 (br. s., 1H) 4.30 (q, J=7.19 Hz, 2H) 2.69 (s, 3H) 1.30 (t, J=7.15 Hz, 3H).

Workup

  1. customwas placed on 100° C.
  2. customfor 1.5 hours
  3. customto give a solid mass
  4. customtriturated with ether
  5. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-95a9bee0f3df4a8abb6d4067962edb8d
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Linked notes

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