Triethylamine → 1-methyl-2-(6-methyl-[1,4]oxazepan-4-yl)-1H-[4,4']bipyrimidinyl-6-one

HRID 515455Notes

Reaction equation

HRID 515455 reaction equation
Cl[C:2]1[N:3]([CH3:15])[C:4](=[O:14])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[N:7]=1.Cl.[CH3:17][CH:18]1[CH2:24][O:23][CH2:22][CH2:21][NH:20][CH2:19]1.C(N(CC)CC)C>O1CCCC1>[CH3:15][N:3]1[C:4](=[O:14])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)[N:7]=[C:2]1[N:20]1[CH2:19][CH:18]([CH3:17])[CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 667185826-Methyl-1,4-oxazepane hydrochloride

Product 1

HCID 667185661-methyl-2-(6-methyl-[1,4]oxazepan-4-yl)-1H-[4,4']bipyrimidinyl-6-oneYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (113 mg, 0.507 mmol) and 6-methyl-[1,4]oxazepane hydrochloride (100 mg, 0.660 mmol) in tetrahydrofuran (1.1 mL) was added triethylamine (154 mg, 1.52 mmol) at room temperature. The mixture was stirred for 15 hours and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was washed with ether and dried under reduced pressure to afford 1-methyl-2-(6-methyl-[1,4]oxazepan-4-yl)-1H-[4,4′]bipyrimidinyl-6-one (A087) as white solid (92.2 mg, 60%).

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. washThe crude product was washed with ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-925f2806f00b4de08f9ad59fb23f2909
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

Loading…