Sodium methanethiolate → 2-(Methylthio)quinazolin-6-ol

HRID 639348Notes

Reaction equation

HRID 639348 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12]C)[CH:8]=2)[N:3]=1.[CH3:14][S-:15].[Na+]>C(O)C.C(Cl)Cl.C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>[CH3:14][S:15][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1

Participants

7

Reactant 2

HCID 4378561Sodium methanethiolateHCID 592548522-Chloro-6-methoxyquinazoline

Product 1

HCID 592548632-(Methylthio)quinazolin-6-ol

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6343EthanethiolSolventHCID 6344DichloromethaneSolventHCID 6451240Aluminum(III) ChlorideSolvent

Procedure

In the alternate reaction Scheme B, above, the 2-chloro-6-methoxyquinazoline 8 is reacted with sodium thiomethoxide in ethanol, dry methylene chloride, ethane thiol and aluminum chloride to obtain the 2-methylthioquinazolin-6-ol 13. The desired substituent, in this case 4-chloro(2-pyridyl)-N-methylcarboxamide, is added to the alcohol group to obtain the corresponding substituted methylthioquinazoline 14. Treatment with 3-chloroperoxybenzoic acid in acetic acid results in the corresponding sulfonyl 15, which is replaced by a desired substituent, in this case 2-naphthylaniline, to obtain the desired compound of the invention, in this case N-methyl-4-{[2-(naphthalen-2-ylamino)-quinazolin-6-yl]oxy}pyridine-2-carboxamide.

Workup

  1. customIn the alternate reaction Scheme B

Sources & evidence

ORD record
ord-4a3d82cf02b743298c2494a2b79abc6a
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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