Ammonia → HCID 135830922, compound

HRID 1826286Notes

Reaction equation

HRID 1826286 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-acetoxy4-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-a0d41d9afcca4a099495814ac743cfce
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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