Toluene → HCID 59286703, compound

HRID 1876023Notes

Reaction equation

HRID 1876023 reaction equation
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([CH3:8])[N:7]=1.[CH2:10]([O:12][C:13]([N:15]=[C:16]=[S:17])=[O:14])[CH3:11].C1(C)C=CC=CC=1>CO>[CH3:8][C:6]1[N:7]=[C:2]2[S:17][C:16]([NH:15][C:13](=[O:14])[O:12][CH2:10][CH3:11])=[N:9][C:3]2=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 85320Ethyl isothiocyanatoformateHCID 98990432-Amino-3-bromo-5-methylpyrazine

Product 1

HCID 59286703HCID 59286703, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-bromo-5-methylpyrazin-2-amine (850 mg, 4.52 mmol) was added ethoxycarbonyl isothiocyanate (0.51 mL, 4.52 mmol) followed by toluene (1 mL). The mixture was placed in a preheated 100° C. oil bath, and within a minute, all the solids had dissolved. After 15 min, all had seized to a solid mass. After an additional 15 minutes, methanol (˜5 mL) was added and the mixture refluxed to digest the solids. The mixture was cooled to rt after 5 minutes and the solids collected by filtration, washing with methanol to give ethyl 6-methylthiazolo[5,4-b]pyrazin-2-ylcarbamate (680 mg, 2.85 mmol, 63.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.48 (br. s., 1H) 8.48 (s, 1H) 4.30 (q, J=7.03 Hz, 2H) 2.56-2.65 (m, 3H) 1.31 (t, J=7.15 Hz, 3H). MS (LC/MS) R.T.=2.10; [M+H]+=239.17.

Workup

  1. customwas placed in a preheated 100° C.
  2. dissolutionwithin a minute, all the solids had dissolved
  3. waitAfter an additional 15 minutes
  4. temperaturethe mixture refluxed
  5. filtrationthe solids collected by filtration
  6. washwashing with methanol

Sources & evidence

ORD record
ord-62470ccc0b984fb9a44d406c6b6a3c60
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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