Acetonitrile → N-tert-Butyl-7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-amine

HRID 2282328Notes

Reaction equation

HRID 2282328 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[N:6][C:7]=1[Cl:8].[C:10]([N:14]=[C:15]=[S:16])([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>CCOC(C)=O.O>[C:10]([NH:14][C:15]1[S:16][C:3]2[N:4]=[CH:5][N:6]=[C:7]([Cl:8])[C:2]=2[N:1]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 11544tert-Butyl isothiocyanateHCID 794345-Amino-4,6-dichloropyrimidine

Product 1

HCID 11572293N-tert-Butyl-7-chloro[1,3]thiazolo[5,4-d]pyrimidin-2-amineYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-Amino-4,6-dichloropyrimidine (9.0 g, 55 mmol), tert-butylisothiocyanate (7.02 g, 61.0 mmol), Cesium Carbonate (39.7 g, 122 mmol) and acetonitrile (200 mL) was stirred at 50° C. for 16 hours. The mixture was allowed to cool to rt. To the mixture, were added water and EtOAc. After being stirred for 30 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (6.45 g, 48%) as a white solid. LCMS: (AA) ES+ 243, 245. 1H NMR (400 MHz, d6-DMSO) δ: 8.71 (bs, 1H), 8.49 (s, 1H), 1.45 (s, 9H).

Workup

  1. temperatureto cool to rt
  2. stirringAfter being stirred for 30 min
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78180f1470f94e19a200893ac774aca2
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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