Hydrochloric Acid → (7-Chloro-2,6-naphthyridin-3-yl)methanol

HRID 468896Notes

Reaction equation

HRID 468896 reaction equation
Cl.[Si]([O:9][CH2:10][C:11]1[N:12]=[CH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][N:17]=[C:16]([Cl:21])[CH:15]=2)(C(C)(C)C)(C)C>O.CO.C(Cl)Cl.CCCCCCC>[Cl:21][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:11]([CH2:10][OH:9])[N:12]=[CH:13]2)=[CH:18][N:17]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 866749683-((Tert-butyldimethylsilyloxy)methyl)-7-chloro-2,6-naphthyridine

Product 1

HCID 86674969(7-Chloro-2,6-naphthyridin-3-yl)methanolYield 90%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

A solution of 5.0M hydrogen chloride in water (0.73 mL) was added to a solution of 3-((tert-butyldimethylsilyloxy)methyl)-7-chloro-2,6-naphthyridine (1.13 g, 3.7 mmol) in methanol (15 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with methylene chloride (150 mL), and washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was suspended in heptane (10 mL) and filtered to provide the title compound as a white powder (645 mg, 90%). 1H NMR (400 MHz, DMSO) δ 9.37 (s, 2H), 8.23 (s, 1H), 8.06 (s, 1H), 5.65 (t, J=5.6 Hz, 1H), 4.78 (d, J=5.6 Hz, 2H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto afford a residue that
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cb9909c15964465e87787467b5c86ddc
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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