Potassium Carbonate → HCID 15729882, compound

HRID 981987Notes

Reaction equation

HRID 981987 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:20]=[C:19](SC)[C:18]([F:23])=[CH:17][N:16]=1)=O)(C)(C)C.ClC1N=C(SC)C(F)=CN=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:23][C:18]1[CH:17]=[N:16][C:15]([N:11]2[CH2:10][C@@H:9]3[CH2:14][C@H:12]2[CH2:13][NH:8]3)=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136082512-Chloro-5-fluoro-4-(methylsulfanyl)pyrimidineHCID 157298792-(t-butyloxycarbonyl)-5-(5-fluoro-4-methylthio-2-pyrimidinyl)-(1S,4S)-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 15729882HCID 15729882, compoundYield 149.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(t-butyloxycarbonyl)-5-(5-fluoro-4-methylthio-2-pyrimidinyl)-(1S,4S)-2,5-diazabicyclo[2.2.1]heptane (4.50 g, 22.73 mmol), 2-chloro-5-fluoro-4-methylthiopyrimidine [4.64 g (87.5% pure), 22.73 mmol], micropulverized K2CO3 (9.40 g, 68.19 mmol), and KI (0.57 g, 3.41 mmol) in 65 mL of MeCN was refluxed for 44 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a minimum amount of H2O. The solution was extracted with CH2Cl2, washed with saturated NaCl solution, dried over K2CO3, filtered and concentrated under reduced pressured. Flash chromatography (Hexane:EtOAc; 4:1) gave the title compound (6.60 g, 85.4%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a minimum amount of H2O
  3. extractionThe solution was extracted with CH2Cl2
  4. washwashed with saturated NaCl solution
  5. dry with materialdried over K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressured

Sources & evidence

ORD record
ord-7f8bd31bfc2a438abe3c8070a4e6f3ba
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

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