Methyl iodide → HCID 59030527, compound

HRID 1619197Notes

Reaction equation

HRID 1619197 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1.[C:20]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:20][O:18][C:17]([C:7]1([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:15][CH2:16]1)=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68902596HCID 68902596, compound

Product 1

HCID 59030527HCID 59030527, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of crude 8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]decane-8-carboxylic acid and K2CO3 (227 mg, 1.64 mmol) in DMF (5 mL) was added MeI (76.7 μl, 1.23 mmol) at 25° C. After being stirred at 25° C. for 15 h, DMF was removed under reduced pressure and the residue was diluted (H2O), extracted (2×EtOAc), and washed (2× brine). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (SiO2, 40-50% EtOAc/Hexanes, gradient elution) gave 8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]decane-8-carboxylic acid methyl ester (170 mg, 0.611 mmol, 74%) as a colorless liquid.

Workup

  1. customDMF was removed under reduced pressure
  2. additionthe residue was diluted (H2O)
  3. extractionextracted (2×EtOAc)
  4. washwashed (2× brine)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue
  8. washby flash chromatography (SiO2, 40-50% EtOAc/Hexanes, gradient elution)

Sources & evidence

ORD record
ord-6838cd1329544af3a39d484e295eb218
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

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