N-Methyl-4-anisidine → HCID 59242113, compound

HRID 1876163Notes

Reaction equation

HRID 1876163 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][CH:18]=1.C([O-])(=O)C.[Na+]>>[Cl:1][C:2]1[N:11]=[C:10]([N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[CH3:24])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 22250N-Methyl-4-anisidineHCID 517045Sodium AcetateHCID 99913972,4-Dichloro-6-methoxyquinazoline

Product 1

HCID 59242113HCID 59242113, compoundYield 98%

Conditions

Temperature
65 °C

Procedure

A mixture of 2,4-dichloro-6-methoxy-quinazoline (0.5g, 2.18 mmol), (4-methoxyphenyl)-methylamine (0.35 g, 2.61 mmol) and sodium acetate (0.21 g, 2.61 mmol) in 8 mL of solvent (THF:water=1:1) was stirred at 60-70° C. for 3 h. The reaction mixture was concentrated and the resulting solid was dissolved in ethyl acetate and transferred to the silica gel pad (30mg) and washed with 40% ethyl acetate/hexane as eluent. The filtrate was concentrated under reduced pressure to give 0.7 g of the clean product (98% yield). 1H NMR (DMSO): δ 7.6 (d, 1H), 7.36-7.31 (m, 3H), 7.08-7.05 (dd, 2H), 6.2 (d, 1H), 3.79 (s, 3H), 3.5 (s, 3H), 3.28(s, 3H). LC/MS: 330, (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe resulting solid was dissolved in ethyl acetate
  3. washwashed with 40% ethyl acetate/hexane as eluent
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-401450e3dcea47baadfb0c6a373503a6
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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