Water → N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine

HRID 906324Notes

Reaction equation

HRID 906324 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([NH2:12])=[N:10][CH:11]=1.[CH:13]1([CH2:18][N:19]([CH2:30][CH3:31])[C:20]2[C:21]([CH:28]=O)=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH:13]1([CH2:18][N:19]([CH2:30][CH3:31])[C:20]2[C:21]([CH2:28][NH:12][C:9]3[N:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][S:2][CH3:1])=[CH:11][N:10]=3)=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 583396535-(2-(Methylthio)ethoxy)pyrimidin-2-amineHCID 866284303-[(Cyclopentylmethyl)(ethyl)amino]-6-methoxypicolinaldehyde

Product 1

HCID 67248264N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amineYield 67%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 5-[2-(methylthio)ethoxy]pyrimidin-2-amine (1.03 g, 5.55 mmol) obtained in Step 1 and 3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypicolinaldehyde (1.60 g, 6.10 mmol) obtained in Step 3 in 1,2-dichloroethane (60 mL) was stirred at room temperature for 10 minutes, and then added with sodium triacetoxyborohydride (1.24 g, 5.83 mmol), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was added with water, and extracted with chloroform— The organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-({3-[(cyclopentylmethyl)(ethyl)amino]-6-methoxypyridin-2-yl}methyl)-5-[2-(methylthio)ethoxy]pyrimidin-2-amine (1.60 g, 67%) as pale yellow oil.

Workup

  1. extractionextracted with chloroform— The organic layers
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a8cf02098b114994bf42ebe52c9e8fe8
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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