Methyl iodide → HCID 59242046, compound

HRID 1876217Notes

Reaction equation

HRID 1876217 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:24])[N:4]=1.[H-].[Na+].ClCC1N=C(NC2C=CC(OCC)=CC=2)C2C(=CC=CC=2F)[N:30]=1.CI>C1COCC1.CCOC(C)=O.CO>[NH2:30][CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[F:24])[N:4]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68516843HCID 68516843, compoundHCID 68518642HCID 68518642, compound

Product 1

HCID 59242046HCID 59242046, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Chloromethyl-5-fluoro-quinazolin-4-yl)-(4-ethoxy-phenyl)-methyl-amine: NaH (60 mg, 1.5 mmol) was added to a solution of (2-chloromethyl-5-fluoro-quinazolin-4-yl)-(4-ethoxy-phenyl)-amine (184 mg, 0.5 mmol) and MeI (0.10 mL) in THF (2 mL) at rt and the reaction stirred for 2 h. MeOH and EtOAc were added. The organics were washed with brine, dried (MgSO4), filtered and concentrated. Purification by MPLC (SiO2, EtOAc/hexanes, 0-100%) provided the desired compound.

Workup

  1. washThe organics were washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by MPLC (SiO2, EtOAc/hexanes, 0-100%)

Sources & evidence

ORD record
ord-17fea928503e494f8100c0b9d9076f12
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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