2,4-Dichloroquinazoline → HCID 59242130, compound

HRID 1876175Notes

Reaction equation

HRID 1876175 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][NH:18][CH3:19].C([O-])(O)=O.[Na+]>Cl.CC(O)C>[Cl:1][C:2]1[N:11]=[C:10]([N:18]([CH2:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][CH3:13])[CH3:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 2528862,4-DichloroquinazolineHCID 516892Sodium BicarbonateHCID 5223022-Methoxy-N-methylbenzylamine

Product 1

HCID 59242130HCID 59242130, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 2,4-dichloro-quinazoline (88 wt %, 525 mg, 2.3 mmol), (2-methoxy-benzyl)-methyl-amine (300 μL, 2.01 mmol) and 1 drop of concd HCl in i-PrOH (8 mL) was reacted for 5 days then concd in vacuo. Satd NaHCO3 (5 mL) was added then the product extracted into CHCl3 (2×4 mL). The organic portion was washed with water (1×3 mL) then dried (MgSO4), filtered through a plug of silica with an EtOAc wash then purified by MPLC (SiO2/0-20% i-PrOH in CHCl3) yielding the title compound as a white solid (247 mg; 39%). 1H NMR (CDCl3) δ 7.83-7.77 (m, 2H), 7.67 (m, 1H), 7.40-7.32 (m, 2H), 7.26 (m, 1H), 7.01 (m, 1H), 6.95 (m, 1H), 4.96 (s, 2H), 3.81 (s, 3H), 3.31 (s, 3H); LC-MS (ESI+; 314 ([M+H]+)).

Workup

  1. customwas reacted for 5 days
  2. extractionthe product extracted into CHCl3 (2×4 mL)
  3. washThe organic portion was washed with water (1×3 mL)
  4. dry with materialthen dried (MgSO4)
  5. filtrationfiltered through a plug of silica with an EtOAc
  6. washwash
  7. customthen purified by MPLC (SiO2/0-20% i-PrOH in CHCl3)

Sources & evidence

ORD record
ord-214264a664b042d48173846e76445952
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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