Diisopropylethylamine → HCID 71283777, compound

HRID 1752424Notes

Reaction equation

HRID 1752424 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:22]([O:24][CH3:25])=[O:23])[N:3]=1.Cl.[NH2:27][C@@H:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30].CCN(C(C)C)C(C)C>C(#N)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:11]2[CH:12]=[CH:13][C:8]([C:6]3[CH:7]=[C:2]([NH:27][C@@H:28]([CH3:33])[C:29]([O:31][CH3:32])=[O:30])[N:3]=[C:4]([C:22]([O:24][CH3:25])=[O:23])[N:5]=3)=[CH:9][CH:10]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 89422485HCID 89422485, compound

Product 1

HCID 71283777HCID 71283777, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of methyl 4-chloro-6-(4-(4-fluorophenoxy)phenyl)pyrimidine-2-carboxylate (0.719 g, 2.00 mmol) in acetonitrile (10 mL) was added (S)-methyl 2-aminopropanoate hydrochloride (0.310 g, 2.22 mmol) and iPr2NEt (0.77 mL, 4.4 mmol). The mixture was heated at 50° C. for 2 h than 80° C. for 6 days. The mixture was evaporated in vacuo and the residue chromatographed over silica gel with 20-60% EtOAc/hexanes. The product fractions were evaporated in vacuo to give (S)-methyl 4-(4-(4-fluorophenoxy)phenyl)-6-((1-methoxy-1-oxopropan-2-yl)amino)pyrimidine-2-carboxylate as a pale tan oil (0.479 g, 1.13 mmol, 56% yield). LC/MS: m/z=426.2 [M+H]+.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue chromatographed over silica gel with 20-60% EtOAc/hexanes
  3. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-6fd2f30802cb4acd8a751f30bddf6db6
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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