Methyl iodide → HCID 22923400, compound

HRID 55043Notes

Reaction equation

[CH3:1][O:2]C1C=C2C(=CC=1OC)N=CN=C2N1CCC(N2C(=O)C3C(=CC=C(O)C=3)NC2=O)CC1.[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][C:45]=1[O:46][CH3:47])[N:42]=[CH:41][N:40]=[C:39]2[N:48]1[CH2:53][CH2:52][CH:51]([N:54]2[C:63](=[O:64])[C:62]3[C:57](=[CH:58][CH:59]=[C:60]([N+]([O-])=O)[CH:61]=3)[NH:56][C:55]2=[O:68])[CH2:50][CH2:49]1.[CH3:69]I.[H-].[Na+]>>[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][C:45]=1[O:46][CH3:47])[N:42]=[CH:41][N:40]=[C:39]2[N:48]1[CH2:53][CH2:52][CH:51]([N:54]2[C:63](=[O:64])[C:62]3[C:57](=[CH:58][CH:59]=[C:60]([O:2][CH3:1])[CH:61]=3)[N:56]([CH3:69])[C:55]2=[O:68])[CH2:50][CH2:49]1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 22923385HCID 22923385, compound2×

HCID 229233993-[1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-nitro-2,4-dioxoquinazoline

Product 1

HCID 22923400HCID 22923400, compoundYield 74%

Procedure

The procedure similar to that described in Example 1 was repeated, except that 251.0 mg (0.56 mmol) of 3-[1-(6,7-dimethoxy-4-quinazolinyl)-4-piperidinyl]-1,2,3,4-tetrahydro-6-hydroxy-2,4-dioxoquinazoline (Compound 102) obtained in Reference Example 13 was used in place of Compound 24 and 3 equivalents of methyl iodide and 3 equivalents of sodium hydride were used. As a result, 197.2 mg (yield: 74%) of Compound 69 was obtained as white crystals.

Workup

customobtained in Reference Example 13

Sources & evidence

ORD record: ord-44e6e079c03049cba677a15bb6ea7be7
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624926

Reaction notes

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