Water → HCID 66613915, compound

HRID 1801960Notes

Reaction equation

HRID 1801960 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH2:7])[CH:3]=1.[I-].[K+].[Cl:10][C:11]1[CH:12]=[C:13]([C:18]([C:20]2[N:29]=[C:28](Cl)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[O:19])[CH:14]=[CH:15][C:16]=1[F:17].O>CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]([C:20]2[N:29]=[C:28]([NH:7][C:4]3[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=3)[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)=[O:19])[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 86649067HCID 86649067, compound

Product 1

HCID 66613915HCID 66613915, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-methyl-1H-pyrazol-3-amine (0.26 g, 2.68 mmol), potassium iodide (0.26 g, 1.57 mmol), and TEA (0.45 mL, 3.23 mmol) in DMF (30 mL) was added (3-chloro-4-fluorophenyl)(4-chloroquinazolin-2-yl)methanone (0.495 g, 1.54 mmol) and the mixture was stirred at rt overnight. Water was added and the precipitated solid was collected by filtration to afford crude (3-chloro-4-fluorophenyl)(4-(5-methyl-1H-pyrazol-3-ylamino)quinazolin-2-yl)methanone (458 mg) which was used directly in the next step. LC-MS (ESI) m/z 382 (M+H)+.

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-9bdc8fd0d148499ab8aef16281706be1
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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