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3-Pyridinecarboxaldehyde → 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanol

HRID 6343
Notes
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Reaction equation

HRID 6343 reaction equation
C([Li])CCC.[CH3:6][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH3:27])[N:11]=1)([CH3:9])[CH3:8].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=[O:35])[CH:29]=1>C1COCC1>[CH3:9][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH2:27][CH:34]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)[OH:35])[N:11]=1)([CH3:6])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 199229904,6-Ditert-butyl-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidineHCID 178418339Butyllithium

Product 1

HCID 190071464,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanolYield 50%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

n-Butyllithium (1.5 mL of 1.6M solution in hexane, 2.4 mmol) is added dropwise to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine (750 mg, 2.4 mmol) in dry THF (12 mL) at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature for 30 minutes and then cooled to -78° C. A solution of pyridine 3-carboxaldehyde (250 mg, 2.4 mmol) in dry THF (1 mL) is added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then is quenched by the addition of saturated aqueous ammonium chloride. The product is extracted into ether. The organic layer is dried (MgSO4) and evaporated to give crude 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3- pyridinyl)- 2-pyrimidineethanol (500 mg, 50%) which is not further purified, but used directly in the next reaction.

Workup

  1. temperaturecooled to -78° C
  2. stirringThe reaction mixture is stirred at room temperature for 3 hours
  3. customis quenched by the addition of saturated aqueous ammonium chloride
  4. extractionThe product is extracted into ether
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f8b7c078c1f34c738ce919fd25bc8ca3
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05248682

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes