Tert-Butylamine → 2-(tert-butylamino)-8-iodo-3-(3-(methylsulfonyl)propyl)quinazolin-4(3H)-one

HRID 1056417Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with 2-chloro-8-iodo-3-(3-(methylsulfonyl)propyl)quinazolin-4(3H)-one (50 mg, 0.117 mmol) and tert-butylamine (0.123 mL, 1.172 mmol) in DMSO (0.5 mL). The reaction mixture was stirred and heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 1 h. The reaction was repeated on 150 mg scale. The reaction mixture were combined and diluted with water (20 mL). The mixture was extracted with CHCl3/iPrOH (4:1, 40 mL×3) and the combined organic layers were washed with water, dried (MgSO4), filtered and concentrated. The residue was purified with silica gel chromatography (eluted with 10-70% EtOAc in Hexanes) to give 2-(tert-butylamino)-8-iodo-3-(3-(methylsulfonyl)propyl)quinazolin-4(3H)-one (108 mg, 50% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 464 (M+1).

Workup

customA glass microwave reaction vessel
extractionThe mixture was extracted with CHCl3/iPrOH (4:1, 40 mL×3)
washthe combined organic layers were washed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified with silica gel chromatography (eluted with 10-70% EtOAc in Hexanes)

Sources & evidence

ORD record: ord-d5885bc664af4846af7a0c3afcfe64b8
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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