4,6-Dichloropyrimidine → HCID 86669604, compound

HRID 1398634Notes

Reaction equation

HRID 1398634 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][O:19][C:20]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][N:21]=1>C(O)CCC>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:26][C:25]2[C:20]([O:19][CH3:18])=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 27374883-Amino-2-methoxypyridine

Product 1

HCID 86669604HCID 86669604, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4,6-dichloropyrimidine (660.04 mg, 4.43 mmol) in 1-butanol (10 mL) was added DIPEA (0.67 ml, 4.03 mmol) followed by 2-methoxypyridin-3-amine (500 mg, 4.03 mmol). The reaction mixture was then heated to 90° C. for 2 hr. The reaction mixture was then concentrated in vacuo and partitioned between DCM and water. A precipitate was removed by filtration and the organics extracted (2×20 ml DCM). The combined organic extracts were then washed with 0.5M HCl (5 ml) and then dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate (300 mg, LC-MS purity=83%); LC-MS: m/z=+236.95/238.90 (M+H)+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompartitioned between DCM and water
  3. customA precipitate was removed by filtration
  4. extractionthe organics extracted (2×20 ml DCM)
  5. washThe combined organic extracts were then washed with 0.5M HCl (5 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-072277d069174d02aa0384041db55c37
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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