Triethylamine → (5-(5-(Quinazolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate

HRID 2108861Notes

Reaction equation

HRID 2108861 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[C:19](=[O:26])[CH:20]=[C:21]([CH2:24][OH:25])[O:22][CH:23]=2)=[N:3][CH:2]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:25][CH2:24][C:21]1[O:22][CH:23]=[C:18]([O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2][N:3]=2)[C:19](=[O:26])[CH:20]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 179757985-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

Product 1

HCID 57629432(5-(5-(Quinazolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 15 (0.53 g, 1.49 mmol) in CH2Cl2 (20 mL) was added at 0° C. triethylamine (252 μL, 1.78 mmol), methanesulfonyl chloride (138 μL, 1.78 mmol). The solution was stirred at RT for 1 h. Dichloromethane (50 mL) was added and the solution was washed with water (2×100 mL), dried over MgSO4, filtered and evaporated. (5-(5-(Quinazolin-4-yloxy)pentyloxy)-4-oxo-4H-pyran-2-yl)methyl methanesulfonate 20 was obtained (0.64 g, 99% yield) as a pale yellow oil.

Workup

  1. washthe solution was washed with water (2×100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-beff927d4cab41918cfc9a84f7aa3a39
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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