Trimethylsilyldiazomethane → HCID 178486866, compound

HRID 890975Notes

Reaction equation

[CH3:1][N:2]([CH3:30])[CH2:3][CH2:4][NH:5][C:6]([NH:21][C:22]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:29])=[N:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([OH:20])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][N:9]=1.[CH3:31][Si](C=[N+]=[N-])(C)C>>[CH3:19][O:18][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][C:14]=1[O:20][CH3:31])[N:11]=[CH:10][N:9]=[C:8]2[NH:7][C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:30])=[N:21][C:22]1[C:23]([CH3:29])=[CH:24][CH:25]=[CH:26][C:27]=1[CH3:28]

Participants

Reactant 2

HCID 167693Trimethylsilyldiazomethane

HCID 178486728HCID 178486728, compound

Product 1

HCID 178486866HCID 178486866, compoundYield 63%

Procedure

Using an analogous procedure to that described in Example 11, N-(2-dimethylaminoethyl)-N′-(2,6-dimethylphenyl)-N″-(7-hydroxy-6-methoxyquinazolin-4-yl)guanidine was reacted with trimethylsilyldiazomethane to give the title compound in 63% yield; NMR Spectrum: (DMSOd6, 100° C.) 2.21 (s, 6H), 2.24 (s, 6H), 2.54 (t, 2H), 3.57 (q, 2H), 3.75 (s, 3H), 3.9 (s, 3H), 7.08 (s, 1H), 7.17 (s, 3H), 7.58 (s, 1H), 8.43 (s, 1H), 10.8 (br s, 1H); Mass Spectrum: M+H+ 423.

Sources & evidence

ORD record: ord-436948b2c67b4480907528889de4bc05
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001904B1

Reaction notes

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