4-Benzylcyclohexanone → 6-Benzyl-5,6,7,8-tetrahydroquinazoline-2,4-diamine
Reaction equation
[C:1]1([CH2:7][CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([NH:17][C:18]([NH2:20])=[NH:19])#[N:16]>>[NH2:20][C:18]1[N:17]=[C:15]([NH2:16])[C:12]2[CH2:13][CH:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:9][CH2:10][C:11]=2[N:19]=1Participants
Procedure
In an alternate method, when n is the bridging group --CH2 --, the 8-phenylmethylene-1,4-dioxaspiro[4.5]decane is treated with acetic acid and water as previously described, yielding the corresponding 4-phenylmethylenecyclohexanone. The cyclohexanone is then reduced with hydrogen gas in the presence of 10% palladium on charcoal (Degussa type), yielding the corresponding 4-phenylmethylcyclohexanol, which is in turn treated with sodium dichromate and sulfudc acid in water, affording the 4-phenylmethylcyclohexanone. The 4-phenylmethylcyclohexanone is then reacted with cyanoguanidine, as previously described, yielding the targeted 2,4-diamino-6-phenylmethyl-5,6,7,8-tetrahydroquinazoline. Example 3 provides a detailed description of how this reaction is conducted.
Sources & evidence
- ORD record
- ord-dbaf92de1b314c03941d9e9bcd256db3
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05712281
Reaction notes
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