2,4,6-Trichloropyrimidine → HCID 59198368, compound

HRID 1920814Notes

Reaction equation

HRID 1920814 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[NH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 811216-Methoxy-3-pyridinylamineHCID 81531Diisopropylethylamine

Product 1

HCID 59198368HCID 59198368, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,4,6-trichloropyrimidine (2.0 mL, 17.4 mmol), 3-amino-6-methoxypyridine (1.5 mL, 19.1 mmol) and diisopropylethylamine (6.1 mL, 34.8 mmol) in acetonitrile (100 mL) was stirred at 55° C. under N2 for 15 hours. The reaction mixture was then partitioned between EtOAc (400 mL) and NaHCO3(sat.) (100 mL). The organic layer was separated, washed with brine (75 mL), dried over Na2SO4, concentrated, and purified by silica gel chromatography (20-30% EtOAc/hexanes) to yield 2,6-dichloro-N-(6-methoxypyridin-3-yl)pyrimidin-4-amine (2.51 g, 53%) as an off-white solid. LCMS (m/z): 270.9 and 272.9 (MH+); 1H NMR (CDCl3): δ 8.13 (d, J=2.7 Hz, 1H), 8.55 (dd, J=8.5, 2.7 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 6.84(bs, 1H), 6.35 (s, 1H), 3.97 (s, 3H).

Workup

  1. customThe reaction mixture was then partitioned between EtOAc (400 mL) and NaHCO3(sat.) (100 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (75 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (20-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-239bf46c90fa4687b2d525936931b939
Source dataset
uspto-grants-2012_05
Patent number
US08173647B2

Reaction notes

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