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Water → (+)-2-{7-[4-(5-methyl-[1,2,4]-oxadiazole-3-yl)phenyl]-[1,4]-oxazepane-4-yl}-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one

HRID 515482
Notes
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Reaction equation

HRID 515482 reaction equation
Cl.[CH3:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[O:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[N:4]=1.Cl[C:22]1[N:27]([CH3:28])[C:26](=[O:29])[CH:25]=[C:24]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][N:31]=2)[N:23]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH3:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]3[O:20][CH2:19][CH2:18][N:17]([C:22]4[N:27]([CH3:28])[C:26](=[O:29])[CH:25]=[C:24]([C:30]5[CH:35]=[CH:34][N:33]=[CH:32][N:31]=5)[N:23]=4)[CH2:16][CH2:15]3)=[CH:12][CH:13]=2)[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 667185737-[4-(5-Methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-[1,4]oxazepane hydrochloride

Product 1

HCID 67281171(+)-2-{7-[4-(5-methyl-[1,2,4]-oxadiazole-3-yl)phenyl]-[1,4]-oxazepane-4-yl}-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one
Yield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a slurry of optically active 7-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-[1,4]oxazepane hydrochloride (0.12 g, 0.41 mmol) and 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.09 g, 0.38 mmol) was added triethylamine (0.21 mL, 1.5 mmol) at room temperature. The mixture was stirred for 20 hours and poured into water. Extractive workup with chloroform was performed and the organic phase was dried over sodium sulfate. Concentration followed by purification of the residue by flash column chromatography on silica gel (chloroform/methanol=100/0 to 90/10 as eluants) yielded (+)-2-{7-[4-(5-methyl-[1,2,4]-oxadiazole-3-yl)phenyl]-[1,4]-oxazepane-4-yl}-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one (A100) (0.09 g, 0.19 mmol, 50%) as yellowish solid.

Workup

  1. dry with materialthe organic phase was dried over sodium sulfate
  2. concentrationConcentration
  3. customfollowed by purification of the residue by flash column chromatography on silica gel (chloroform/methanol=100/0 to 90/10 as eluants)

Sources & evidence

ORD record
ord-fb84f6e221a341afbb5af10603562120
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09108957B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes