Dichloromethane → HCID 89782161, compound

HRID 1056365Notes

Reaction equation

HRID 1056365 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Br:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14](Cl)[N:13]([CH2:18][CH3:19])[C:12]2=[O:20].C(Cl)Cl>O>[Br:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[C:14]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[N:13]([CH2:18][CH3:19])[C:12]2=[O:20]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 89782153HCID 89782153, compound

Product 1

HCID 89782161HCID 89782161, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tert-butylamine (1.1 mL, 10.43 mmol) and 8-bromo-2-chloro-3-ethylquinazolin-4(3H)-one (100 mg, 0.348 mmol, 481c) was sealed and set stirring for 3 h at 80° C. The reaction was cooled to RT, diluted with water, and extracted with DCM. The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure giving a pale yellow solid. The material was taken up DCM, adsorbed onto silica, and purified on 4 g SiO2 (eluent: 0-100% EtOAc/hexanes over 20 min, RediSep Gold). The product containing fractions were combined and concentrated under reduced pressure to a colorless residue (52 mg, 46%). m/z (ESI, +ve) 323.9 (M+H)+.

Workup

  1. customwas sealed
  2. temperatureThe reaction was cooled to RT
  3. extractionextracted with DCM
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customgiving a pale yellow solid
  8. custompurified on 4 g SiO2 (eluent: 0-100% EtOAc/hexanes over 20 min, RediSep Gold)
  9. additionThe product containing fractions
  10. concentrationconcentrated under reduced pressure to a colorless residue (52 mg, 46%)

Sources & evidence

ORD record
ord-08fb9e4731624ce88b0b5d3a3c5eef02
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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