Isopropylamine → HCID 89781877, compound

HRID 1056271Notes

Reaction equation

HRID 1056271 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]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:7]2=[O:19].[CH:20]([NH2:23])([CH3:22])[CH3:21]>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:23][CH:20]([CH3:22])[CH3:21])[N:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:7]2=[O:19]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 89782278HCID 89782278, compound

Product 1

HCID 89781877HCID 89781877, compoundYield 103%

Conditions

Temperature
80 °C

Procedure

A slurry of 8-bromo-2-chloro-3-(pyridin-3-yl)quinazolin-4(3H)-one (403b, 0.20 g, 0.594 mmol) and isopropylamine (2.04 mL, 23.77 mmol) was sealed and heated in an 80° C. oil bath for 1 h. The reaction was partitioned between sat'd aq. NaHCO3 and DCM. The aqueous layer was extracted with DCM 2 times, and the combined organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 8-bromo-2-(isopropylamino)-3-(pyridin-3-yl)quinazolin-4(3H)-one (0.22 g, 0.612 mmol, 103% yield) as a light yellow foam. 1H NMR (400 MHz, CDCl3) δ ppm 8.83 (1H, d, J=3.5 Hz), 8.60 (1H, br. s.), 8.08 (1H, dd, J=7.8, 1.6 Hz), 7.94 (1H, dd, J=7.7, 1.5 Hz), 7.66-7.75 (1H, m), 7.60 (1H, dd, J=8.0, 4.9 Hz), 7.04 (1H, t, J=7.8 Hz), 4.32-4.49 (1H, m), 3.80 (1H, d, J=6.3 Hz), 1.23 (6H, m). m/z (ESI, +ve) 359.0/361.0 (M+H)+.

Workup

  1. customThe reaction was partitioned between sat'd aq. NaHCO3 and DCM
  2. extractionThe aqueous layer was extracted with DCM 2 times
  3. dry with materialthe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9e3d43f00f44ea28c8c15bf09656f11
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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