2-Naphthoic acid → HCID 59514551, compound

HRID 1159654Notes

Reaction equation

HRID 1159654 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:12]=[C:11]([N:13]([CH3:15])[CH3:14])[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][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:56]1[C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[CH:59]=[CH:58][C:57]=1[C:66](O)=[O:67]>CN(C=O)C.O>[CH3:14][N:13]([CH3:15])[C:11]1[C:10]([CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][N:8]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:66]([C:57]3[CH:58]=[CH:59][C:60]4[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=4)[CH:56]=3)=[O:67])=[CH:22][CH:21]=2)[N:12]=1

Participants

6

Reactant 3

HCID 71232-Naphthoic acidHCID 2724699PyBOPHCID 59514489HCID 59514489, compound

Product 1

HCID 59514551HCID 59514551, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution containing methyl [2-(4-aminobenzyl)-4-(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 treated with 2-naphthoic acid (0.062 g, 0.36 mmol). The reaction mixture was stirred for 3 hours before diluting with water. The thus quenched reaction mixture was extracted with EtOAc and the combined organic extracts was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the crude product methyl {4-(dimethylamino)-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate.

Workup

  1. customThe thus quenched reaction mixture
  2. extractionwas extracted with EtOAc
  3. washthe combined organic extracts was washed sequentially with 0.5N HCl, saturated NaHCO3, and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9aaa1b45df7d40cb9fdc1232f448d945
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

Loading…