Chlorotrimethylsilane → HCID 118024047, compound

HRID 2171783Notes

Reaction equation

HRID 2171783 reaction equation
BrC(Br)C.C[Si](Cl)(C)C.[C:10]([O:18][CH2:19]I)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl[C:22]1[C:23]2[N:31]=[C:30]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[S:29][C:24]=2[N:25]=[C:26]([CH3:28])[N:27]=1>C1COCC1.[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]([O:18][CH2:19][C:22]1[C:23]2[N:31]=[C:30]([CH:32]3[CH2:37][CH2:36][C:35]([CH3:39])([CH3:38])[CH2:34][CH2:33]3)[S:29][C:24]=2[N:25]=[C:26]([CH3:28])[N:27]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 112011,1-DibromoethaneHCID 10015543Iodomethyl BenzoateHCID 118023992HCID 118023992, compound

Product 1

HCID 118024047HCID 118024047, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

Under an argon atmosphere, to a suspension of zinc powder (7.5 g) in THF (50 mL) were added dibromoethane (200 μL) and trimethylsilylchloride (200 μL), and then a solution of iodomethyl benzoate (15 g) in THF (50 mL) was added thereto, followed by stirring at room temperature for 1 hour. Then, a solution of 7-chloro-2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidine (10.9 g) in THF (50 mL) and Pd(PPh3)4 (4.25 g) were added thereto, followed by stirring at room temperature for 15 hours. The reaction mixture was filtered through Celite and then concentrated under reduced pressure. To the residue was added a 1 M aqueous NH4Cl solution, followed by extraction with EtOAc. To the organic layer were added MgSO4 and basic silica gel, followed by stirring, filtrating, and then concentrating under reduced pressure. The residue was purified by silica gel column (hexane/EtOAc) to obtain [2-(4,4-dimethylcyclohexyl)-5-methyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl]methyl benzoate (13.8 g).

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added a 1 M aqueous NH4Cl solution
  5. extractionfollowed by extraction with EtOAc
  6. additionTo the organic layer were added MgSO4 and basic silica gel
  7. stirringby stirring
  8. filtrationfiltrating
  9. concentrationconcentrating under reduced pressure
  10. customThe residue was purified by silica gel column (hexane/EtOAc)

Sources & evidence

ORD record
ord-0186f5e0c40647d0993a9eeb7f712cb9
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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