Ammonia → HCID 135830922, compound

HRID 641746Notes

Reaction equation

HRID 641746 reaction equation
C([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([Cl:15])=[N:10][CH:11]=[N:12]2)=[C:7]([O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:6]=1)(=O)C.N>CO>[Cl:15][C:9]1[C:8]2[C:13](=[CH:14][C:5]([OH:4])=[CH:6][C:7]=2[O:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22140714HCID 22140714, compound

Product 1

HCID 135830922HCID 135830922, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-acetoxy-4-chloro-5-cyclopentyloxyquinazoline (1 g), a saturated methanolic ammonia solution (10 ml) and methanol (10 ml) was stirred at ambient temperature for 30 minutes. The mixture was evaporated and the residue was triturated under water. The resultant solid was isolated, washed with water and dried under vacuum to give 4-chloro-5-cyclopentyloxy-7-hydroxyquinazoline (0.67 g); NMR Spectrum: (DMSOd6) 1.6-1.75 (m, 2H), 1.75-1.85 (m, 2H), 1.85-2.05 (m, 4H), 5.0 (m, 1H), 6.72 (d, 1H), 6.8 (d, 1H), 8.7 (s, 1H); Mass Spectrum: M+H+ 265.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated under water
  3. customThe resultant solid was isolated
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fbc17872fe3e4055b8e3982764df27b9
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

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