Potassium Iodide → HCID 46865781, compound

HRID 625740Notes

Reaction equation

HRID 625740 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([F:21])([F:20])[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:3]=1.[I-].[K+].CCN(C(C)C)C(C)C.[CH3:33][C:34]1[NH:38][N:37]=[C:36]([NH2:39])[CH:35]=1>CN(C=O)C>[F:20][C:12]([F:21])([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:4]1[N:3]=[C:2]([NH:39][C:36]2[CH:35]=[C:34]([CH3:33])[NH:38][N:37]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 72942926HCID 72942926, compound

Product 1

HCID 46865781HCID 46865781, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-(difluoro(4-fluorophenyl)methyl)quinazoline (0.150 g, 0.487 mmol) in DMF (2 mL) at rt were added potassium iodide (0.081 g, 0.487 mmol), DIEA (0.093 mL, 0.535 mmol) and 5-methyl-1H-pyrazol-3-amine (0.048 g, 0.487 mmol). After stirring the reaction mixture at rt overnight, the reaction was quenched by adding water (15 mL). The precipitate was collected by filtration and washed with H2O. The crude solid was triturated with MeOH. 2-(Difluoro(4-fluorophenyl)methyl)-N-(5-methyl-1H-pyrazol-3-yl)quinazolin-4-amine was obtained as an off-white solid (0.125 g, 69%). 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 6.31 (s, 1H), 7.34 (m, 2H), 7.68 (m, 3H), 7.87 (m, 2H), 8.68 (m, 1H), 10.69 (s, 1H), 12.20 (s, 1H); LC-MS (ESI) m/z 370 (M+H)+.

Workup

  1. customthe reaction was quenched
  2. additionby adding water (15 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O
  5. customThe crude solid was triturated with MeOH

Sources & evidence

ORD record
ord-d1c79842a98640489dd082c33767a2ec
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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