4-Chloro-5-methyl-6-(4-methylphenyl)pyrimidine → Ethyl (2-methyl-4-{[[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl](propyl)amino]methyl}phenoxy)acetate

HRID 1269661Notes

Reaction equation

HRID 1269661 reaction equation
ClC1C(C)=C(C2C=CC(C)=CC=2)N=CN=1.[CH3:16][C:17]1[CH:29]=[C:28]([CH2:30][N:31]([C:35]2[C:40]([CH3:41])=[C:39]([C:42]3[CH:47]=[CH:46][C:45]([C:48](F)(F)F)=[CH:44][CH:43]=3)[N:38]=[CH:37][N:36]=2)[CH2:32][CH2:33][CH3:34])[CH:27]=[CH:26][C:18]=1[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH3:16][C:17]1[CH:29]=[C:28]([CH2:30][N:31]([C:35]2[C:40]([CH3:41])=[C:39]([C:42]3[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=3)[N:38]=[CH:37][N:36]=2)[CH2:32][CH2:33][CH3:34])[CH:27]=[CH:26][C:18]=1[O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

3

Reactant 2

HCID 184484024-Chloro-5-methyl-6-(4-methylphenyl)pyrimidineHCID 58622851Ethyl (2-methyl-4-{[{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}(propyl)amino]methyl}phenoxy)acetate

Product 1

HCID 58622853Ethyl (2-methyl-4-{[[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl](propyl)amino]methyl}phenoxy)acetate

Procedure

Using 4-chloro-5-methyl-6-(4-methylphenyl)pyrimidine (153 mg, 0.7 mmol) and the synthetic procedure described for Intermediate 80. Purification by Biotage™ chromatography (Si, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (80 mg).

Workup

  1. customPurification by Biotage™ chromatography (Si, 40 g)
  2. washeluting 9:1 cyclohexane

Sources & evidence

ORD record
ord-c7d56863da994f16b312a797f92d55eb
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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