Tert-Butylamine → HCID 89782287, compound

HRID 1056436Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[N:8]([CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:7]2=[O:19].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.N12CCCN=C1CCCCC2.[C:58]([NH2:62])([CH3:61])([CH3:60])[CH3:59]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:62][C:58]([CH3:61])([CH3:60])[CH3:59])[N:8]([CH2:13][CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[C:7]2=[O:19]

Participants

Conditions

Temperature: 40 °C

Procedure

A glass microwave reaction vessel was charged with 8-bromo-3-(2-(methylsulfonyl)ethyl)quinazoline-2,4(1H,3H)-dione (200 mg, 0.576 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (382 mg, 0.864 mmol, Sigma Aldrich) in DMF (2 mL) followed by 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.172 mL, 1.152 mmol, Sigma Aldrich). The reaction mixture was stirred for 5 min. tert-butylamine (0.30 mL, 2.88 mmol) was added. The reaction was stirred at 40° C. for 4 h. The mixture was diluted with EtOAc (30 mL) and washed with water, brine, dried (MgSO4), filtered and concentrated. The residue was purified with silica gel chromatography (eluted with 0-10% EtOAc in DCM) to give 8-bromo-2-(tert-butylamino)-3-(2-(methylsulfonyl)ethyl)quinazolin-4(3H)-one (516c; 90 mg, 0.224 mmol, 39% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 402 (M+1).

Workup

customA glass microwave reaction vessel
additionwas added
washwashed with water, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified with silica gel chromatography (eluted with 0-10% EtOAc in DCM)

Sources & evidence

ORD record: ord-9fbb601aa01647da87ecd1fc597b305f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394297B2

Reaction notes

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