Methyl iodide → HCID 59242089, compound

HRID 1876200Notes

Reaction equation

HRID 1876200 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][CH3:22])=[CH:17][C:16]=2[F:23])[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Cl.ClCC1N=C(NC2C=CC(OC)=CC=2F)C2C(=CC=CC=2)[N:28]=1.[H-].[Na+].CI>C1COCC1.CO>[NH2:28][CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[F:23])[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68514632HCID 68514632, compoundHCID 68520871HCID 68520871, compound

Product 1

HCID 59242089HCID 59242089, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2-Chloromethyl-quinazolin-4-yl)-(2-fluoro-4-methoxy-phenyl)-methyl-amine: A solution of (2-chloromethyl-quinazolin-4-yl)-(2-fluoro-4-methoxy-phenyl)-amine hydrochloride (291 mg, 0.82 mmol) in THF (4 mL) was treated with NaH (130 mg, 3.12 mmol), followed by MeI (0.26 mL, 4.2 mmol). The reaction was stirred for 2 h, diluted with MeOH and concentrated. Purification by MPLC (SiO2, EtOAc/hexanes, 0-100%) gave the desired compound. 1H NMR (CDCl3) δ 7.84 (d, 1H), 7.55-7.65 (m, 1H), 7.02-7.17 (m, 3H), 6.68-6.79 (m, 2H), 4.74 (s, 2H), 3.85 (s, 3H), 3.58 (s, 3H); LC-MS (ESI+; 332 ([M+H]+)).

Workup

  1. concentrationconcentrated
  2. customPurification by MPLC (SiO2, EtOAc/hexanes, 0-100%)

Sources & evidence

ORD record
ord-6495dfeec39d4cc0b04bdd3bba871ebe
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

Loading…