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

HRID 515476Notes

Reaction equation

HRID 515476 reaction equation
CC1N=C(C2C=CC([CH:13]3[O:19][CH2:18][CH2:17][N:16]([C:20]4[N:25]([CH3:26])[C:24](=[O:27])[CH:23]=[C:22]([C:28]5[CH:33]=[CH:32][N:31]=[CH:30][N:29]=5)[N:21]=4)[CH2:15][CH2:14]3)=CC=2)ON=1.Cl.[O:35]1[C:39]([C:40]2[CH:45]=[CH:44][C:43](C3COCCNC3)=[CH:42][CH:41]=2)=[N:38][CH:37]=[N:36]1>>[CH3:26][N:25]1[C:24](=[O:27])[CH:23]=[C:22]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][N:29]=2)[N:21]=[C:20]1[N:16]1[CH2:15][CH:14]([C:43]2[CH:42]=[CH:41][C:40]([C:39]3[O:35][N:36]=[CH:37][N:38]=3)=[CH:45][CH:44]=2)[CH2:13][O:19][CH2:18][CH2:17]1

Participants

3

Reactant 2

HCID 67281351(+)-2-{7-[4-(3-Methyl-[1,2,4]-oxadiazole-5-yl)phenyl]-[1,4]-oxazepane-4-yl}-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-oneHCID 672830996-(4-[1,2,4]Oxadiazol-5-yl-phenyl)-[1,4]oxazepane hydrochloride

Product 1

HCID 667187631-Methyl-2-[6-(4-[1,2,4]oxadiazol-5-yl-phenyl)-[1,4]oxazepan-4-yl]-1H-[4,4']bipyrimidinyl-6-one

Procedure

1-Methyl-2-[6-(4-[1,2,4]oxadiazol-5-yl-phenyl)-[1,4]oxazepan-4-yl]-1H-[4,4′]bipyrimidinyl-6-one was prepared by the same procedure as that of 2-{7-[4-(3-Methyl-[1,2,4]-oxadiazole-5-yl)phenyl]-[1,4]-oxazepane-4-yl}-3-methyl-6-pyrimidin-4-yl-3H-pyrimidin-4-one except for utilizing 6-(4-[1,2,4]Oxadiazol-5-yl-phenyl)-[1,4]oxazepane hydrochloride instead of 7-[4-(3-Methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-[1,4]oxazepane hydrochloride. 1-Methyl-2-[6-(4-[1,2,4]oxadiazol-5-yl-phenyl)-[1,4]oxazepan-4-yl]-1H-[4,4′]bipyrimidinyl-6-one (A080) was obtained as white solid (0.02 g, 0.04 mmol, 50%).

Sources & evidence

ORD record
ord-c5ea1b299bc1459ea6371b0450ce2335
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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