Water → HCID 59514494, compound

HRID 1159666Notes

Reaction equation

HRID 1159666 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:12]=[C:11]([Cl:13])[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]([CH3:21])[CH3:20])[N:8]=2)=[CH:4][CH:3]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[CH:59][C:58]=1[C:67](O)=[O:68].O>CN(C=O)C>[Cl:13][C:11]1[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([N:19]([CH3:20])[CH3:21])[N:8]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:67]([C:58]3[CH:59]=[CH:60][C:61]4[C:66](=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH:57]=3)=[O:68])=[CH:23][CH:22]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 71232-Naphthoic acidHCID 2724699PyBOPHCID 59514486Methyl 2-[(4-aminophenyl)methyl]-4-chloro-6-(dimethylamino)-5-pyrimidineacetate

Product 1

HCID 59514494HCID 59514494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl [2-(4-aminobenzyl)-4-chloro-6-(dimethylamino)pyrimidin-5-yl]acetate (0.090 g, 0.30 mmol) and PyBOP (0.187 g, 0.36 mmol) in anhydrous DMF (1 mL) at room temperature was added 2-naphthoic acid (0.062 g, 0.36 mmol). The resulting reaction mixture was stirred at room temperature for 3 hours at which time water was added and the resulting aqueous phase was extracted with EtOAc. The combined organic extracts was sequentially washed with 0.5N HCl, saturated NaHCO3, and brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give methyl {4-chloro-6-(dimethylamino)-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. extractionthe resulting aqueous phase was extracted with EtOAc
  4. washThe combined organic extracts was sequentially washed with 0.5N HCl, saturated NaHCO3, and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5af8c92d28824fb5804ab4be65ff41db
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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