3-Amino-5,5-dimethyl-2-cyclohexen-1-one → 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(2-pyrimidinyloxy)-phenyl]-1,8(2H,5H)-acridinedione

HRID 1275833Notes

Reaction equation

HRID 1275833 reaction equation
[NH2:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.CO[CH:13](OC)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH:15]=1>>[CH3:8][C:6]1([CH3:9])[CH2:7][C:2]2[NH:1][C:2]3[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[C:3]=3[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]4[N:22]=[CH:23][CH:24]=[CH:25][N:26]=4)[CH:15]=3)[C:3]=2[C:4](=[O:10])[CH2:5]1

Participants

3

Reactant 2

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-oneHCID 221178593-(2-Pyrimidinyloxy)-benzaldehyde dimethyl acetal

Product 1

HCID 221178473,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(2-pyrimidinyloxy)-phenyl]-1,8(2H,5H)-acridinedione

Procedure

Reaction of 3-amino-5,5-dimethyl-2-cyclohexen-1-one with 3-(2-pyrimidinyloxy)-benzaldehyde dimethyl acetal in an analogous manner to that described in Example 1 gave 3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-9-[3-(2-pyrimidinyloxy)-phenyl]-1,8(2H,5H)-acridinedione. Crystallization from dimethylformamide/water gave a pale yellow crystalline solid of melting point 220-221° C.

Sources & evidence

ORD record
ord-9b51c37675cb4540943dc256eec8ae42
Source dataset
uspto-grants-2000_12
Patent number
US06162918

Reaction notes

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