Pyridine → HCID 86634084, compound

HRID 1041760Notes

Reaction equation

HRID 1041760 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][NH:16][CH3:17])[C:5]([Cl:18])=[CH:4][N:3]=1.C(O[C:23](=[O:25])[CH3:24])(=O)C.N1C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][N:16]([CH3:17])[C:23](=[O:25])[CH3:24])[C:5]([Cl:18])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86634085HCID 86634085, compound

Product 1

HCID 86634084HCID 86634084, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2,5-dichloro-pyrimidin-4-yl)-(2-methylaminomethyl-phenyl)-amine in THF (25 mL) was treated with acetic anhydride (60 mg, 0.59 mmol, 1.2 eq) and pyridine (50 mg, 0.63 mmol, 1.3 eq.) at 25° C. for 2 h. The solvent was evaporated and the residue was purified by semi-preparative HPLC to give N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-benzyl]-N-methyl-acetamide (40 mg, 0.12 mmol, 24%). 1H NMR (300 MHz, CDCl3): δ 8.22 (s, 1H), 7.73 (d, 1H), 7.3 (m, 3H), 4.48 (s, 2H), 3.24 (s, 3H), 2.12 (s, 3H); MS (m/e) 325 (M+1).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by semi-preparative HPLC

Sources & evidence

ORD record
ord-76e36a9e08c44fdaa1528092edc3812b
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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