Diisopropylethylamine → (2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-pyridin-3-yl)-amine

HRID 1687559Notes

Reaction equation

HRID 1687559 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)C(C)C)(C)C.[Cl:19][C:20]1[N:25]=[C:24](Cl)[C:23]([Cl:27])=[CH:22][N:21]=1>C(O)(C)C>[Cl:19][C:20]1[N:25]=[C:24]([NH:9][C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=2)[C:23]([Cl:27])=[CH:22][N:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 27374883-Amino-2-methoxypyridine

Product 1

HCID 86633975(2,5-Dichloro-pyrimidin-4-yl)-(2-methoxy-pyridin-3-yl)-amineYield 56.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-methoxy-pyridin-3-ylamine (1.00 g, 0.00806 mol) and N,N-diisopropylethylamine (2.1 mL, 0.012 mol) in isopropyl alcohol (20 mL) was added 2,4,5-trichloropyrimidine (1.0 mL, 0.0089 mol). The mixture was stirred at room temperature overnight. The suspension was filtered, the solid was washed with isopropanol (10 mL) then hexane (20 mL). The solids were dried under vacuum to provide (2,5-dichloro-pyrimidin-4-yl)-(2-methoxy-pyridin-3-yl)-amine (1.23 g, 56%) as a white solid. LC/MS (ESI+): 271.40 (M+H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with isopropanol (10 mL)
  3. customThe solids were dried under vacuum

Sources & evidence

ORD record
ord-07025bdeabf142a9b725cf8546f3259c
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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