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Dimethylformamide → 4-Amino-6-benzyloxy-2-chloro-7-methoxyquinazoline

HRID 1004001
Notes
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Reaction equation

HRID 1004001 reaction equation
CN(C)C=O.P(Cl)(Cl)([Cl:8])=O.[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:30][CH3:31])=[C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14](O)[N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.C(OCC)(=O)C>[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:30][CH3:31])=[C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14]([Cl:8])[N:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178486884HCID 178486884, compound

Product 1

HCID 109799944-Amino-6-benzyloxy-2-chloro-7-methoxyquinazolineYield 27%

Reagents, catalysts & solvents 2

HCID 3776
Isopropanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dimethyl formamide (7.9 ml, 0.10 mol) was added dropwise to phosphorus oxychloride (47.9 ml, 0.52 mol) with stirring. After 10 minutes, 4-amino-6-benzyloxy-2-hydroxy-7-methoxyquinazoline (16.4 g, 0.055 mol) was added portionwise and the resulting mixture heated at 90° C. for 1.5 hours, then cooled and poured into ethyl acetate (750 ml). The mixture was neutralised by the portionwise addition of aqueous sodium carbonate and the phases were separated. The organic layer was evaporated to dryness and the residue combined with the organic phase which was then treated with aqueous sodium hydroxide to basify (pH10) and the mixture was heated at 90° C. for 2 hours. After cooling, the mixture was partitioned between dichloromethane (11) and water (11), the organic phase washed with water, dried over MgSO4 and evaporated to give a pale yellow solid. Trituration with isopropanol afforded the subtitle compound as a colourless solid (4.64 g, 27%). Rf 0.64 (ethyl acetate:methanol 95:5, v/v). MS m/z 316, 318 (MH+).

Workup

  1. temperaturecooled
  2. customthe phases were separated
  3. customThe organic layer was evaporated to dryness
  4. additionwas then treated with aqueous sodium hydroxide
  5. temperaturethe mixture was heated at 90° C. for 2 hours
  6. temperatureAfter cooling
  7. customthe mixture was partitioned between dichloromethane (11) and water (11)
  8. washthe organic phase washed with water
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customto give a pale yellow solid

Sources & evidence

ORD record
ord-686472a7b0f348518a4461246acc1ab0
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048864

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes