Triethylamine → 1-methyl-2-[2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholin-4-yl]-1H-[4,4']bipyrimidinyl-6-one

HRID 1896177Notes

Reaction equation

HRID 1896177 reaction equation
Cl.[C:2]1([C:8]2[O:12][N:11]=[C:10]([CH:13]3[O:18][CH2:17][CH2:16][NH:15][CH2:14]3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]1[C:25](=[O:26])[CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][N:28]=2)[N:22]=[C:21]1N1CCOC(C2ON=C(C3C=CC=CC=3)N=2)C1.C(N(CC)CC)C>O1CCCC1>[CH3:19][N:20]1[C:25](=[O:26])[CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][N:28]=2)[N:22]=[C:21]1[N:15]1[CH2:16][CH2:17][O:18][CH:13]([C:10]2[N:9]=[C:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:12][N:11]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 577987881-methyl-2-(2-(3-phenyl-[1,2,4]oxadiazol-5-yl)-morpholin-4-yl)-1H-[4,4']bipyrimidinyl-6-one2×HCID 668424982-(5-Phenyl-1,2,4-oxadiazol-3-yl)morpholine hydrochloride2×

Product 1

HCID 577987871-methyl-2-[2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholin-4-yl]-1H-[4,4']bipyrimidinyl-6-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the resulting 2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholine hydrochloride (intermediate 28) in tetrahydrofuran (6.0 ml) was added with 2-chloro-3-methyl-6-(pyrimidine-4-yl)pyrimidin-4-one (intermediate 1, 260 mg, 2.34 mmol) and triethylamine (1.81 ml, 13.0 mmol), and the reaction mixture was stirred at room temperature for 2 hours. The solution was partitioned between water and chloroform, and the organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel (eluent; 5% methanol in chloroform) to afford 1-methyl-2-[2-(5-phenyl-[1,2,4]oxadiazol-3-yl)-morpholin-4-yl]-1H-[4,4′]bipyrimidinyl-6-one (compound 2 in Table 1, 749 mg, 64%, 2 steps) as solid

Workup

  1. customThe solution was partitioned between water and chloroform
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography on silica gel (eluent; 5% methanol in chloroform)

Sources & evidence

ORD record
ord-20f1c53d8c984981ab625a000ffe04be
Source dataset
uspto-grants-2013_08
Patent number
US08518939B2

Reaction notes

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