Potassium Carbonate → [2-(2-Amino-6-chloropyrimidin-4-ylsulfanyl)ethyl]carbamic acid tert-butyl ester

HRID 1811747Notes

Reaction equation

HRID 1811747 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][SH:25])([CH3:19])([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[C:16]([O:20][C:21](=[O:26])[NH:22][CH2:23][CH2:24][S:25][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([NH2:1])[N:7]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 655222-Amino-4,6-dichloropyrimidineHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiol

Product 1

HCID 59224716[2-(2-Amino-6-chloropyrimidin-4-ylsulfanyl)ethyl]carbamic acid tert-butyl esterYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of commercially available 2-amino-4,6-dichloropyrimidine (428 mg, 2.61 mmol), potassium carbonate (361 mg, 2.61 mmol), N,N-dimethylformamide (5.0 ml), and (2-mercaptoethyl)carbamic acid tert-butyl ester (356 mg, 2.0 mmol) was stirred in a reaction vessel at room temperature for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, and extracted with ethyl acetate. The organic layer was separated, and then sequentially washed with a saturated aqueous ammonium chloride solution and a saturated aqueous sodium chloride solution. The organic solution was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=5:1 to 2:1) to yield [2-(2-amino-6-chloropyrimidin-4-ylsulfanyl)ethyl]carbamic acid tert-butyl ester (548 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washsequentially washed with a saturated aqueous ammonium chloride solution
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=5:1 to 2:1)

Sources & evidence

ORD record
ord-56224cc1531b48d5a8fcd03635f8dfde
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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