Methylamine → 6-Methylamino-4-(quinolin-6-yloxy)-pyrimidine

HRID 2264570Notes

Reaction equation

HRID 2264570 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.[CH3:19][NH2:20]>C1COCC1>[CH3:19][NH:20][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 576000846-(6-Chloropyrimidin-4-yloxy)quinoline

Product 1

HCID 675302226-Methylamino-4-(quinolin-6-yloxy)-pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7.83 g (30.4 mMol) of 6-chloro-4-(quinolin-6-yloxy)-pyrimidine (step 1.1) and 121 ml of a 1 N MeNH2 in THF is stirred for 7.5 h in a sealed vessel. After addition of 30 g of SiO2, the mixture is concentrated and the resulting powder put on top of a chromatograph column (SiO2; EtOAc). Eluation (EtOAc→EtOAc/EtOH 50:1→20:1→9:1) gives the title compound: m.p.: 173° C.; MS: [M+1]+=253; Anal.: C,H,N.

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-f370fdbe95694c01aed9946453f0ded5
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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