2-Naphthoic acid → Methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetate

HRID 2422164Notes

Reaction equation

HRID 2422164 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[C:6]([CH3:24])=[N:7][C:8]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[N:9][C:10]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH:59]1[C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH:62]=[CH:61][C:60]=1[C:69](O)=[O:70].C(N(CC)C(C)C)(C)C>C1COCC1.O>[CH3:24][C:6]1[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:25])=[C:10]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[N:9]=[C:8]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:69]([C:60]3[CH:61]=[CH:62][C:63]4[C:68](=[CH:67][CH:66]=[CH:65][CH:64]=4)[CH:59]=3)=[O:70])=[CH:21][CH:22]=2)[N:7]=1

Participants

7

Reactant 4

HCID 71232-Naphthoic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59514524Methyl[2-(4-aminobenzyl)-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate

Product 1

HCID 59514539Methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetateYield 36.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl[2-(4-aminobenzyl)-4-methyl-6-pyrrolidin-1-ylpyrimidin-5-yl]acetate (0.034 g, 0.10 mmol) in THF (1 mL) at room temperature was treated with PyBOP (0.052 g, 0.10 mmol), 2-naphthoic acid (0.019 g, 0.11 mmol), and N,N-diisopropylethylamine (0.017 mL, 0.10 mmol). After stirring at room temperature for 17 hours, the reaction mixture was poured into water and extracted with EtOAc. The combined organic extracts was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The remaining residue was chromatographed over silica gel eluting with 60% EtOAc in CH2Cl2 to give methyl {4-methyl-2-[4-(2-naphthoylamino)benzyl]-6-pyrrolidin-1-ylpyrimidin-5-yl}acetate (0.018 g, 36% yield) as a yellow oil.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe remaining residue was chromatographed over silica gel eluting with 60% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-d80c2ccf90c94b66aad6df796da19011
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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