Water → HCID 59514494, compound

HRID 2422154Notes

Reaction equation

HRID 2422154 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[C:6]([Cl:22])=[N:7][C:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[N:9][C:10]=1[N:11]([CH3:13])[CH3:12].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:22][C:6]1[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:23])=[C:10]([N:11]([CH3:12])[CH3:13])[N:9]=[C:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][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:19][CH:20]=2)[N:7]=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-da2ecb3ef7cb4b7e8e76cf85e705c2f5
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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