Ammonium Hydroxide → HCID 178433360, compound

HRID 1710809Notes

Reaction equation

HRID 1710809 reaction equation
I.[Cl:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]([CH3:15])[NH:6][C:7](SC)=[N:8]2.[OH-].[NH4+:17]>C(#N)C.C(O)(C(F)(F)F)=O>[Cl:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]([CH3:15])[NH:6][C:7]([NH2:17])=[N:8]2

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 178503338HCID 178503338, compound

Product 1

HCID 178433360HCID 178433360, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
130 °C

Procedure

5-Chloro-4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (100 mg, 0.28 mmol) was suspended in a mixture of ammonium hydroxide (1 ml, 25% in H2O) and acetonitrile (1 ml) and heated in a microwave oven to 130° C. (15 min) and subsequently to 170° C. (30 min). The title compound (35 mg, 62%) was isolated from the reaction mixture by preparative, reverse-phase HPLC (YMC CombiPrep C18 column 50×20 mm, solvent gradient 5-95% CH3CN in 0.1% TFA(aq) over 6.0 min, λ=230 nm, flow rate 40 ml/min) as a white solid.

Workup

  1. customsubsequently to 170° C.
  2. custom(30 min)

Sources & evidence

ORD record
ord-2b447037860e40dba23ae0b94373cea9
Source dataset
uspto-grants-2010_09
Patent number
US07790732B2

Reaction notes

Loading…