HCID 19705197, compound → HCID 131719464, compound

HRID 727155Notes

Reaction equation

HRID 727155 reaction equation
C1([Si:7]([CH3:16])([CH3:15])[CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)C=CC=CC=1.[C:17]([NH:19][C:20]([NH2:22])=[NH:21])#[N:18]>>[NH2:21][C:20]1[N:19]=[C:17]([NH2:18])[C:9]2[CH:8]([SiH:7]([CH3:15])[CH3:16])[CH:13]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:12][CH2:11][C:10]=2[N:22]=1

Participants

3

Reactant 2

HCID 19705197HCID 19705197, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 131719464HCID 131719464, compound

Procedure

When the bridging group n is --Si(CH3)2 --, the Grignard reagent of 8-bromo-1,4-dioxaspiro[4.5]decane is reacted with, for example, chlorodimethylphenylsilane, affording 8-phenyldimethylsilyl-1,4-dioxaspiro[4.5]decane. The 1,4-dioxaspiro functional group is then cleaved from the so-prepared molecule with acetic acid and water, yielding the corresponding 4-(phenyldimethylsilyl)cyclohexanone. The cyclohexanone is then reacted with cyanoguanidine, affording the target 2,4-diamino-6-phenyldimethylsilyl-5,6,7,8-tetrahydroquinazoline. Example 14 provides a detailed description of how this reaction is conducted.

Sources & evidence

ORD record
ord-56b19dd821764042b389432198eadc7b
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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