2,4-Dichloropyrimidine → HCID 17981132, compound

HRID 347759Notes

Reaction equation

HRID 347759 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[F:18][C:19]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:20]=1[NH2:21]>C(O)CCC.C(Cl)Cl>[F:18][C:19]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:20]=1[NH:21][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1

Participants

6

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 2629702-Fluoro-5-methylaniline

Product 1

HCID 17981132HCID 17981132, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2,4-Dichloropyrimidine (7.0 g, 47 mmol) was dissolved in n-butanol (5 ml), followed by addition of DIPEA (9.0 ml, 51.7 mmol), then 2-fluoro-5-methylaniline (5.3 ml, 47 mmol). The mixture was heated at 100° C. overnight, and then allowed to cool to ambient temperature. The mixture was evaporated to give an oil, which was taken up in DCM (250 ml) and washed with water (3×50 ml), brine (50 ml), dried over MgSO4 and evaporated to give an orange oil. This was purified by column chromatography eluting with EtOAc:isohexane (10:90) to give the title product as a white solid (2.40 g, 21%). NMR (300 MHz): 2.3 (s, 3H), 6.7 (d, 1H), 7.0 (m, 1H), 7.2 (m, 1H), 7.5 (d, 1H), 8.1 (d, 1H), 9.7 (s, 1H); m/z: (ES+) 237.9 (MH+).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe mixture was evaporated
  3. customto give an oil, which
  4. washwashed with water (3×50 ml), brine (50 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto give an orange oil
  8. customThis was purified by column chromatography
  9. washeluting with EtOAc:isohexane (10:90)

Sources & evidence

ORD record
ord-1def1f864b9d4ab6893adde1405b2219
Source dataset
uspto-grants-2007_02
Patent number
US07176212B2

Reaction notes

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