Ammonia → HCID 178488376, compound

HRID 1710818Notes

Reaction equation

HRID 1710818 reaction equation
I.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11](SC)[NH:10][CH:9]2[CH3:16].[NH3:17]>C(#N)C.C(N(CC)CC)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([NH2:17])[NH:10][CH:9]2[CH3:16]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178488380HCID 178488380, compound

Product 1

HCID 178488376HCID 178488376, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 8-methoxy-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (610 mg, 1.7 mmol) in a mixture of acetonitrile (6 ml) and aqueous ammonia (25%, 1.2 ml) was heated in a sealed tube on a shaker for 48 h at 80° C. The title compound (158 mg, 46%, MS: m/e=192.1 [M+H+]) was isolated from the reaction mixture by preparative, reverse-phase HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 1-99% CH3CN in 0.05% triethylamine (aq) over 5.0 min, λ=230 nm, flow rate 40 ml/min) as a solid.

Sources & evidence

ORD record
ord-25539684142d421abd8b4641341751a2
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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