Water → HCID 10363608, compound

HRID 973587Notes

Reaction equation

HRID 973587 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[N:20]=[C:19]2[N:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33])=O)C.O.[OH-].[Na+]>C1COCC1>[OH:9][CH2:10][CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH3:31])[N:20]=[C:19]2[N:32]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54435189HCID 54435189, compound

Product 1

HCID 10363608HCID 10363608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.27 g, 7.1 mmol) was added to dry distilled THF (50 ml) and the mixture stirred in an ice-bath under dry nitrogen. A solution of 8-(ethoxycarbonylmethoxy)-4-(N-methylphenylamino)-2-[(2-methylphenyl)amino]quinazoline (2.4 g, 5.43 mmol) in dry THF (30 ml) was added dropwise at such a rate as to keep the reaction temperature below 5°. The mixture was then allowed to freely reach room temperature and stirred for three hours. Water was carefully added followed by a little 40% NaOH. Two layers were produced and this mixture was extracted (×2) with ethyl acetate. The combined organic extracts were worked with water (×3) and brine, dried (Na2SO4) and evaporated to give an oil which crystallised on scratching to a yellow solid (1.9 g).

Workup

  1. customto dry
  2. distillationdistilled THF (50 ml)
  3. customthe reaction temperature below 5°
  4. customwas then allowed to freely reach room temperature
  5. stirringstirred for three hours
  6. customTwo layers were produced
  7. extractionthis mixture was extracted (×2) with ethyl acetate
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customto give an oil which
  11. customcrystallised

Sources & evidence

ORD record
ord-988dfc161fd04abb88322b5623a712a0
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

Loading…