Potassium Iodide → HCID 178470279, compound

HRID 625759Notes

Reaction equation

HRID 625759 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:3]=1.[I-].[K+].CCN(C(C)C)C(C)C.[NH:29]1[CH:33]=[CH:32][C:31]([NH2:34])=[N:30]1>CN(C=O)C.O>[NH:29]1[CH:33]=[CH:32][C:31]([NH:34][C:2]2[C:11]3[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=3)[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:3]=2)=[N:30]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 86649053Ethyl 4-chloro-7-iodoquinazoline-2-carboxylateHCID 178418806HCID 178418806, compound

Product 1

HCID 178470279HCID 178470279, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-chloro-7-iodoquinazoline-2-carboxylate (0.138 g, 0.38 mmol) in DMF (2 mL) at rt under argon were added potassium iodide (0.069 g, 0.42 mmol), DIEA (0.079 mL, 0.45 mmol), and 1H-pyrazol-3-amine (0.038 g, 0.46 mmol). The mixture was stirred at rt overnight then diluted with H2O (15 mL). The precipitate was collected by filtration, washed with H2O, and dried under high vacuum for several hours to afford ethyl 4-(1H-pyrazol-3-ylamino)-7-iodoquinazoline-2-carboxylate as a yellow solid (0.130 g, 84%). 1H NMR (300 MHz, DMSO-d6) δ 1.34 (t, 3H), 4.38 (q, 2H), 7.14 (m, 1H), 7.72 (m, 1H), 7.94 (d, 1H), 8.28 (d, 1H), 8.48 (d, 1H), 10.92 (s, 1H), 12.58 (s, 1H); LC-MS (ESI) m/z 410 (M+H)+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with H2O
  3. customdried under high vacuum for several hours

Sources & evidence

ORD record
ord-639a4e3e39ca4ca2b13256cf5f8dc50a
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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