Sodium Carbonate → HCID 24863242, compound

HRID 2092283Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[C:23](I)[C:24]([CH3:28])=[CH:25][CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[CH3:30][NH:31][C:32]1[N:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37](B3OC(C)(C)C(C)(C)O3)[CH:38]=2)[N:33]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[C:23]([C:37]5[CH:38]=[C:39]6[C:34](=[CH:35][CH:36]=5)[N:33]=[C:32]([NH:31][CH3:30])[N:41]=[CH:40]6)[C:24]([CH3:28])=[CH:25][CH:26]=4)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 180 °C

Procedure

2 M Aqueous sodium carbonate (857 μl, 1.7 mmol), tetrakis(triphenylphosphine)palladium (0) (99 mg, 86 μmol), N-(2,3-dihydro-1H-inden-5-yl)-8-iodo-7-methylquinazolin-4-amine hydrochloride (250 mg, 571 μmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (326 mg, 1142 μmol) and dioxane (5 mL) were added to a microwave vial. The reaction mixture was heated in a microwave at 180° C. for 20 min. The solid residue was filtered off through Celite® and washed with methanol and DCM. The filtrate was concentrated and purified by flash chromatography (0-10% MeOH in DCM) to give 6-(4-(2,3-dihydro-1H-inden-5-ylamino)-7-methylquinazolin-8-yl)-N-methylquinazolin-2-amine as an off-white amorphous solid. MS (M+H)+ 433.

Workup

filtrationThe solid residue was filtered off through Celite®
washwashed with methanol and DCM
concentrationThe filtrate was concentrated
custompurified by flash chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-d385b6e148d54bed8bf615070705e9db
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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