Aniline → HCID 89781929, compound

HRID 1056076Notes

Reaction equation

HRID 1056076 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19](Cl)[N:18]=[CH:17]2.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[NH4+].[Cl-]>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[C:19]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[N:18]=[CH:17]2

Participants

6

Reactant 4

HCID 6115AnilineHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 457900618-Bromo-2-chloroquinazoline

Product 1

HCID 89781929HCID 89781929, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

LHMDS (1.0M in THF; 4.11 mL, 4.11 mmol) was added to a solution of 8-bromo-2-chloroquinazoline (Ark Pharm, Inc., Libertyville, Ill.; 500 mg, 2.053 mmol) and aniline (0.337 mL, 3.70 mmol) in THF (10 mL) at 0° C., and the resulting solution was stirred at 0° C. for 10 min. Saturated aq. NH4Cl (10 mL) was added, and the resulting mixture was partitioned between EtOAc (50 mL) and additional saturated aq. NH4Cl (30 mL). The organic layer was separated, washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 8-bromo-N-phenylquinazolin-2-amine (616 mg, 2.052 mmol, 100% yield) as a yellow solid: m/z (ESI, +ve) 300.0 (M+H)+.

Workup

  1. customthe resulting mixture was partitioned between EtOAc (50 mL) and additional saturated aq. NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (silica gel, 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-186b83400f264668b58b6ad833df54ab
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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