Tert-Butylamine → HCID 89793968, compound

HRID 1056411Notes

Reaction equation

HRID 1056411 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[N:8]([CH:13]1[CH2:16][CH2:15][CH2:14]1)[C:7]2=[O:17].[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19]>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]([CH:13]1[CH2:16][CH2:15][CH2:14]1)[C:7]2=[O:17]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 89793970HCID 89793970, compound

Product 1

HCID 89793968HCID 89793968, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 8-bromo-2-chloro-3-cyclobutylquinazolin-4(3H)-one (294.7 mg, 0.94 mmol), tert-butylamine (Aldrich; 1.5 mL, 14.27 mmol), and NMP (0.5 mL) was heated in a sealed microwave vial at 120° C. for 30 min. The reaction mixture was then partitioned between EtOAc (60 mL) and water (40 mL). The organic layer was separated and sequentially washed water (40 mL) and brine (40 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(tert-butylamino)-3-cyclobutylquinazolin-4(3H)-one (266 mg, 0.759 mmol, 81% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87 (1H, dd, J=7.6, 1.2 Hz), 7.84 (1H, dd, J=7.8, 1.4 Hz), 6.98 (1H, t, J=7.8 Hz), 5.88 (1H, s), 4.47-4.60 (1H, m), 2.54-2.64 (2H, m), 2.06-2.20 (2H, m), 1.56-1.66 (2H, m), 1.52 (9H, s). m/z (ESI, +ve) 349.9/352.0 (M+H)+.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc (60 mL) and water (40 mL)
  2. customThe organic layer was separated
  3. dry with materialsequentially washed water (40 mL) and brine (40 mL), then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7f4a298086e4772bf460a08c8dc6108
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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