Acetaldehyde → 1-(2-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-yl)ethanol

HRID 2098816Notes

Reaction equation

HRID 2098816 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([Li])CCC.[CH:22](=[O:24])[CH3:23]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[O:10][C:9]([CH:22]([OH:24])[CH3:23])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 568337412-Chloro-4-morpholinofuro[3,2-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 866184461-(2-Chloro-4-morpholinofuro[3,2-d]pyrimidine-6-yl)ethanolYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 from Example 19 (0.3 mmol) dissolved in THF (3 mL) at −78° C. was added 1.6M solution of n-butyllithium (0.39 mmol). The reaction mixture was stirred for 30 mins at which point acetaldehyde (1.2 mmol) was added. The reaction was stirred for one hour and quenched with ice and allowed to warm to room temperature. The aqueous layer was extracted with methylene chloride and the organic layer was filtered through sodium sulfate. The organic phase was concentrated to yield 1-(2-chloro-4-morpholinofuro[3,2-d]pyrimidine-6-yl)ethanol (72 mg).

Workup

  1. additionwas added
  2. customquenched with ice
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. filtrationthe organic layer was filtered through sodium sulfate
  5. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-58c09f4807cf4ac79fc1ba7786ed83d4
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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