Water → HCID 178437722, compound

HRID 1458670Notes

Reaction equation

HRID 1458670 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([C:19]#[C:20][Si](C)(C)C)[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].O>O1CCCC1.C1(C)C=CC=CC=1>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([Cl:18])=[C:16]([C:19]#[CH:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 178445672HCID 178445672, compound

Product 1

HCID 178437722HCID 178437722, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.64 g (1.76 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-5-chloro-6-trimethylsilylethynylpyrimidine (Example 27) was dissolved in 20 ml of tetrahydrofuran, and 2 ml of a 1.0M solution of tetrabutylammonium fluoride in tetrahyrofuran were added at 0° C. The mixture was stirred at room temperature for 2 hours, diluted with toluene and exracted by stirring with sodium hydrogen carbonate solution and water. The organic phase was dried and concentrated. Chromatography on silica gel left 0.44 g (86.0% of theory) of a colorless oil which gradually solidified.

Workup

  1. customThe organic phase was dried
  2. concentrationconcentrated
  3. waitChromatography on silica gel left 0.44 g (86.0% of theory) of a colorless oil which

Sources & evidence

ORD record
ord-c026137962fd4c1095f13b64cc32df08
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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