Iodine → HCID 86630620, compound

HRID 602386Notes

Reaction equation

CC1C=CC=CC=1B(O)O.N[C:12]1[N:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([O:29][CH3:30])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:18]=2)[N:13]=1.[I:31]I.[I-].[Cs+].N(OCCC(C)C)=O>COCCOC.[Cu](I)I>[I:31][C:12]1[N:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([O:29][CH3:30])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:18]=2)[N:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a similar manner to Example 4, 2-amino-7-methoxy-6-(2-methylphenyl)quinazoline was obtained using Compound A2 and 2-methylphenylboronic acid. The obtained 2-amino-7-methoxy-6-(2-methylphenyl)quinazoline (4.38 g, 16.5 mmol) was dissolved in DME (165 mL) and the solution was added with iodine (1.05 g, 8.3 mmol), cesium iodide (4.3 g, 16.5 mmol), isoamyl nitrite (13.3 mL, 99 mmol) and copper iodide (3.1 g, 16.5 mmol), followed by stirring at 80° C. for 7 hours. After an insoluble matter was filtered off from the reaction mixture, the solvent was evaporated under reduced pressure. The residue was added with aqueous saturated sodium thiosulfate solution and 28% aqueous ammonia and the obtained crystal was collected by filtration to obtain 2-iodo-7-methoxy-6-(2-methylphenyl)quinazoline (5.76 g, 93%) as a crude product. In a similar manner to Reference Example 4 and Example 19, Compound 174 was obtained using the above-obtained 2-iodo-7-methoxy-6-(2-methylphenyl)quinazoline and 4-heptylamine.

Workup

filtrationAfter an insoluble matter was filtered off from the reaction mixture
customthe solvent was evaporated under reduced pressure
additionThe residue was added with aqueous saturated sodium thiosulfate solution and 28% aqueous ammonia
filtrationthe obtained crystal was collected by filtration

Sources & evidence

ORD record: ord-c7a31f24283c413ea8b1931dc2aaeea3
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906522B2

Reaction notes

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