6-Bromo-4-[3-methyl-4-(2-pyridylmethoxy)anilino]quinazoline dihydrochloride salt → 4-[3-Methyl-4-(2-pyridylmethoxy)anilino]-6-(2-thienyl)quinazoline

HRID 361363Notes

Reaction equation

HRID 361363 reaction equation
Cl.Cl.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][N:8]=[C:7]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[C:17]([CH3:29])[CH:16]=1.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1B(OC(C)C)OC(C)C>>[CH3:29][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)[NH:14][C:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)[CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 224783866-Bromo-4-[3-methyl-4-(2-pyridylmethoxy)anilino]quinazoline dihydrochloride saltHCID 22478406HCID 22478406, compound

Product 1

HCID 224783694-[3-Methyl-4-(2-pyridylmethoxy)anilino]-6-(2-thienyl)quinazolineYield 70%

Procedure

Using an analogous procedure to that described in Example 5, 6-bromo-4-[3-methyl-4-(2-pyridylmethoxy)anilino]quinazoline dihydrochloride salt was reacted with di-isopropyl 2-thienylboronate to give 4-[3-methyl-4-(2-pyridylmethoxy)anilino]-6-(2-thienyl)-quinazoline in 70% yield, m.p. 205°-206° C.;

Sources & evidence

ORD record
ord-1aa8ff6b5df04408bc372926734df92f
Source dataset
uspto-grants-1999_02
Patent number
US05866572

Reaction notes

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