Potassium thiocyanate → 1-Benzyl-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazoline-2-thione

HRID 641833Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:11][C:10]=1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:30][C:31]#[N:32].[K+]>C(O)(=O)C>[CH2:1]([N:8]1[C:9]2[C:10](=[CH:11][C:12]([O:15][CH2:16][C:17]#[CH:18])=[CH:13][CH:14]=2)[C:19]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[N:32][C:31]1=[S:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 140 mg (0.365 mmol) (2-benzylamino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone in 5 ml acetic acid is added 68 mg (0.695 mmol) potassium thiocyanate. The reaction is stirred for two days at 60° C. The solvent is removed and the residue is extracted with water/dichloromethane. After evaporation of the organic phase the crude product is purified by flash-chromatography (MeOH/CH2Cl2, 1:9) to give 25 mg (16%) of a yellow oil.

Workup

customThe solvent is removed
extractionthe residue is extracted with water/dichloromethane
customAfter evaporation of the organic phase the crude product
customis purified by flash-chromatography (MeOH/CH2Cl2, 1:9)

Sources & evidence

ORD record: ord-4019bd812d74429f85bb6645d476b6a3
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696216B2

Reaction notes

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