3-(Chloromethyl)pyridine → HCID 131721043, compound

HRID 1459408Notes

Reaction equation

HRID 1459408 reaction equation
[C:1]12([N:11]3[C:16]([CH2:17][CH:18]([CH:24]=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=[N:13][CH2:12]3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC[O-].[Na+].[Cl:30][CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.CCOC(C)=O.CCCCCC>CCO>[ClH:30].[ClH:30].[C:1]12([N:11]3[C:16]([CH2:17][C:18]([CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)([CH:24]=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=[N:13][CH2:12]3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

6

Reactant 4

HCID 183583-(Chloromethyl)pyridineHCID 2723922Sodium ethoxideHCID 21226206Ethyl acetate hexaneHCID 131721045HCID 131721045, compound

Product 1

HCID 131721043HCID 131721043, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

The procedure described in Example 140B was followed with a solution of 3-N-adamantan-1-yl-3-oxo-2-pyrimidin4-ylmethyl-propanoic acid, ethyl ester [prepared as described in Example 144] (0.225 g, 0.629 mmol) in EtOH (3 mL), a 21% by weight solution of NaOEt in EtOH (0.306 mL, 0.818 mmol), and a solution of 3-chloromethylpyridine (0.088 g, 0.692 mmol) in EtOH (1 mL) except that the reaction was heated at 60° C. overnight (16 hours). After flash chromatography (75 to 100% EtOAc-hexane), the title compound, free base (0.119 g, 42%) was obtained as a yellow solid. A portion of the free base (0.039 g, 0.087 mmol) was treated with ethanolic HCl as described in Example 140C to give the dihydrochloride salt (0.030 g, 66%) as a light yellow solid.

Sources & evidence

ORD record
ord-1a58b2966e004c4b9ee3dee2a89a9f24
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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