Acetone → HCID 59593058, compound

HRID 2098620Notes

Reaction equation

HRID 2098620 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.[CH3:22][C:23]([CH3:25])=[O:24]>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]([C:23]([OH:24])([CH3:25])[CH3:22])=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 568337412-Chloro-4-morpholinofuro[3,2-d]pyrimidineHCID 178418339Butyllithium

Product 1

HCID 59593058HCID 59593058, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-chloro-4-morpholinofuro[3,2-d]pyrimidine 38 (60 mg, 1.0 eq) dissolved in THF (2.5 ml) at −78° C. was added 1.6M solution of n-butyllithium (0.20 ml, 1.3 eq, 1.6M in hexanes). Reaction mixture was stirred at −78° C. for 30 minutes. Acetone (0.07 ml, 4.0 eq) was added and reaction mixture was allowed to warm up to −40° C. and stirred for 1 h. The crude reaction mixture was concentrated and purified by reverse phase HPLC to afford 2-(2-chloro-4-morpholinofuro[3,2-d]pyrimidin-6-yl)propan-2-ol 46. MS (Q1) 298 (M)+.

Workup

  1. customReaction mixture
  2. customreaction mixture
  3. temperatureto warm up to −40° C.
  4. stirringstirred for 1 h
  5. customThe crude reaction mixture
  6. concentrationwas concentrated
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-27e74563ad4a410599a16345636f7ec2
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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