Solketal → HCID 14776421, compound

HRID 520490

Reaction equation

HRID 520490 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].Cl[C:13]1[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1>C1COCC1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][C:13]2[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=2)[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 7528SolketalHCID 24758Sodium hydrideHCID 3457522-Chloro-4-aminopyrimidine

Product 1

HCID 14776421HCID 14776421, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of solketal 58 (34.4 g, 260 mmol) in THF (150 mL) was added NaH (10.4 g, 260 mmol) at room temperature and the mixture stirred for 1 h. 2-chloro-4-aminopyrimidine 97 (15.0 g, 115 mmol) was then added, and the mixture was stirred at 70° C. for 48 h. The reaction mixture was concentrated and the crude residue was purified by flash chromatography (dichloromethane:methanol=15:1-10:1) to give 98 (18.2 g, 70% yield) as an oil. The acetonide protecting group could be removed after coupling with the appropriate aniline by treatment with EtOH/3 N HCl (4:1) at reflux for 12 h.

Workup

  1. stirringthe mixture was stirred at 70° C. for 48 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude residue was purified by flash chromatography (dichloromethane:methanol=15:1-10:1)

Sources & evidence

ORD record
ord-aa4df939c7c242ba906436663f2ebe95
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Linked notes

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