Chlorotrimethylsilane → HCID 86591873, compound

HRID 1592289Notes

Reaction equation

HRID 1592289 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:12]=[C:11]([O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[OH:20])[N:10]=[CH:9][N:8]=1.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23].[Cl-].[NH4+]>C(N(CC)CC)C>[Cl:6][C:7]1[CH:12]=[C:11]([O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]2[O:20][Si:22]([CH3:25])([CH3:24])[CH3:23])[N:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86591872HCID 86591872, compound

Product 1

HCID 86591873HCID 86591873, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To 3.2 ml of tetrahydrofuran were added 0.37 g of 4-chloro-6-(cis-2-hydroxycyclohexyloxy)pyrimidine and 0.45 ml of triethylamine, to which 0.25 ml of chlorotrimethylsilane was slowly added dropwise with stirring at 0° C. After stirring at room temperature for 3 hours, the reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.5 g of 4-chloro-6-(cis-2-trimethylsilanyloxycyclohexyloxy)pyrimidine.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionextracted three times with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dbcb41cf58e64033a56d5ee6101c3c87
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

Loading…