1,4-Dioxa-8-azaspiro(4.5)decane → 8-(6-Methylpyrimidin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 451466Notes

Reaction equation

HRID 451466 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl[C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14][N:13]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[CH3:18][C:16]1[N:15]=[CH:14][N:13]=[C:12]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)[CH:17]=1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 81531DiisopropylethylamineHCID 5817964-Chloro-6-methylpyrimidine

Product 1

HCID 673433738-(6-Methylpyrimidin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,4-dioxa-8-azaspiro[4.5]decane (3.04 g, 2.72 mL, 21.2 mmol), 4-chloro-6-methylpyrimidine (3.00 g, 23.4 mmol) and N,N-diisopropylethylamine (4.12 g, 5.56 mL, 31.8 mmol) in dioxane (50 mL) was heated to 140° C. in the microwave for 40 minutes. The reaction mixture was concentrated, then directly purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane). The title compound was obtained as orange oil (4.64 g, 93%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdirectly purified by flash chromatography (silica gel, 70 g, 0% to 15% MeOH/NH4OH (9:1) in dichloromethane)

Sources & evidence

ORD record
ord-8080e3df9131470aabde4fb05ec7a6bb
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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