N1,N1-bis(2-methoxyethyl)-3-methylbutane-1,3-diamine → 2((4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)amino)-8-iodo-3-methylquinazolin-4(3H)-one

HRID 1056358Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:12][CH2:13][O:14][CH3:15])[CH2:6][CH2:7][C:8]([CH3:11])([NH2:10])[CH3:9].[I:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[C:24](S(C)=O)[N:23]([CH3:30])[C:22]2=[O:31]>CC(O)(C)C>[CH3:15][O:14][CH2:13][CH2:12][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:6][CH2:7][C:8]([NH:10][C:24]1[N:23]([CH3:30])[C:22](=[O:31])[C:21]2[C:26](=[C:17]([I:16])[CH:18]=[CH:19][CH:20]=2)[N:25]=1)([CH3:11])[CH3:9]

Participants

Conditions

Temperature: 120 °C

Procedure

A glass microwave reaction vessel was charged with N1,N1-bis(2-methoxyethyl)-3-methylbutane-1,3-diamine (50 mg, 0.229 mmol) and 8-iodo-3-methyl-2-(methylsulfinyl)quinazolin-4(3H)-one (700b; 80 mg, 0.229 mmol) in tBuOH (0.5 mL). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc.) at 120° C. for 45 min. Similarly another two batches (50 mg and 170 mg) were carried out. The three batches were combined and the solvent was removed. The residue was purified with silica gel chromatography (eluted with 0-5% MeOH in DCM) to give 2((4-(bis(2-methoxyethyl)amino)-2-methylbutan-2-yl)amino)-8-iodo-3-methylquinazolin-4(3H)-one (210 mg, 0.42 mmol). MS (ESI, pos. ion) m/z: 503 (M+1).

Workup

customA glass microwave reaction vessel
customthe solvent was removed
customThe residue was purified with silica gel chromatography (eluted with 0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-3f71d11e621148d7b6753e4cbcbbb4d4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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