Isopropanol → N-(2,3-dihydro-1H-inden-5-yl)-8-iodo-7-methylquinazolin-4-amine hydrochloride

HRID 2092282Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH2:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:11][C:12]1[C:21]2[C:16](=[C:17]([I:23])[C:18]([CH3:22])=[CH:19][CH:20]=2)[N:15]=[CH:14][N:13]=1.CC(O)C>CCOC(C)=O>[ClH:11].[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:12]3[C:21]4[C:16](=[C:17]([I:23])[C:18]([CH3:22])=[CH:19][CH:20]=4)[N:15]=[CH:14][N:13]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

2,3-Dihydro-1H-inden-5-amine (109 mg, 821 μmol), 4-chloro-8-iodo-7-methylquinazoline (250 mg, 821 μmol) and IPA (5 mL) were added to microwave-vial. The reaction mixture was heated at 110° C. for 10 min. A precipitate formed upon cooling. The crude product was diluted with EtOAc (20 mL), filtered, washed twice with EtOAc (20 mL) and air-dried to give N-(2,3-dihydro-1H-inden-5-yl)-8-iodo-7-methylquinazolin-4-amine hydrochloride (311 mg, 87%) as an amorphous off-white solid. MS (M+H)+ 402.

Workup

customA precipitate formed
temperatureupon cooling
filtrationfiltered
washwashed twice with EtOAc (20 mL)
customair-dried

Sources & evidence

ORD record: ord-4836f89861564e24bb3dba7f6fc63000
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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