Sodium Hydroxide → 4-Chloro-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinazoline

HRID 643851Notes

Reaction equation

HRID 643851 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[N:18]=[C:17](O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>>[Cl:22][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([C:6]2[S:7][CH:8]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=2)[N:18]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178439803HCID 178439803, compound

Product 1

HCID 591654524-Chloro-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinazoline

Conditions

Temperature
100 °C

Procedure

Compound 50 (100 mg, 0.37 mmol) was added to phosphorous oxychloride (2 mL) and heated to 100° C. for 2 h. The reaction mixture was then poured on ice with vigorous stirring and made basic with NaOH (aq). The resulting slurry was extracted with ether (3×20 mL) and the combined organic phases were dried (MgSO4) and filtered. Removal of the solvent in vacuo afforded the title compound in quantitative yield. LC/MS>95%, m/z (ESI+)=290 (MH+).

Workup

  1. additionThe reaction mixture was then poured on ice
  2. extractionThe resulting slurry was extracted with ether (3×20 mL)
  3. dry with materialthe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-829c8a4d35f8430f97d2a65e40513871
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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