Imidazole → HCID 86711135, compound

HRID 1472625Notes

Reaction equation

HRID 1472625 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH:14]([OH:15])[C:7]2=[N:6][C:5]=1[CH3:16].N1C=CN=C1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>CN(C=O)C>[Si:26]([O:15][CH:14]1[C:7]2=[N:6][C:5]([CH3:16])=[C:4]([CH2:3][CH2:2][Cl:1])[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13]1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 155471943-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 86711135HCID 86711135, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (1.0 g, 4.12 mmol) in DMF (5 mL) was treated with 1H-imidazole (701.24 mg, 64.66 mmol), followed by a solution of t-butyldimethylchlorosilane (683.12 mg, 4.53 mmol) in DMF (1 mL). After stirring for 18 h at room temperature, the solvents were removed under vacuum and the residue was taken up in dichloromethane/water (10 mL/10 mL) with addition of a spatula of potassium carbonate. The aqueous layer was extracted with dichloromethane (three times 10 mL). The combined organic fractions were dried over Na2SO4, filtered, and the solvent was removed under vacuum. The crude mixture was used without further purification in the next step. (ESI-MS (M+1) 357)

Workup

  1. customthe solvents were removed under vacuum
  2. additionthe residue was taken up in dichloromethane/water (10 mL/10 mL) with addition of a spatula of potassium carbonate
  3. extractionThe aqueous layer was extracted with dichloromethane (three times 10 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customThe crude mixture was used without further purification in the next step

Sources & evidence

ORD record
ord-2b28730d6a59407a88955457b5773253
Source dataset
uspto-grants-2015_04
Patent number
US09012648B2

Reaction notes

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