2-Amino-4,6-dichloropyrimidine → HCID 51353725, compound

HRID 2367274Notes

Reaction equation

HRID 2367274 reaction equation
CCN(C(C)C)C(C)C.Cl.[CH3:11][C@H:12]1[NH:17][CH2:16][C@@H:15]([CH2:18][OH:19])[O:14][CH2:13]1.[NH2:20][C:21]1[N:26]=[C:25](Cl)[CH:24]=[C:23]([Cl:28])[N:22]=1>CC#N>[NH2:20][C:21]1[N:26]=[C:25]([N:17]2[C@H:12]([CH3:11])[CH2:13][O:14][C@H:15]([CH2:18][OH:19])[CH2:16]2)[CH:24]=[C:23]([Cl:28])[N:22]=1

Participants

5

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 513579591227911-03-6

Product 1

HCID 51353725HCID 51353725, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

In a 2-5 mL microwave vessel Hunig's base (0.59 mL, 3.35 mmol) was added to [(2S,5R)-5-methyl-2-morpholinyl]methanol hydrochloride (208 mg, 1.12 mmol) in CH3CN (3 mL), and then 2-amino-4,6-dichloropyrimidine (174 mg, 1.06 mmol) was added. The mixture was heated with stirring in a microwave reactor at 160° C. for 1 hour. HPLC indicated complete conversion. The mixture was filtered through a 0.45 um filter disc, evaporated, and the product was purified further by chomatography (Analogix SF25-40 g silica column) eluting with 2-5% CH3OH—CHCl3 to afford the title compound (258 mg) as a white foam. LC-MS (ES) m/z=260 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. filtrationThe mixture was filtered through a 0.45 um
  3. filtrationfilter disc
  4. customevaporated
  5. customthe product was purified further by chomatography (Analogix SF25-40 g silica column)
  6. washeluting with 2-5% CH3OH—CHCl3

Sources & evidence

ORD record
ord-150e27b893b84c379f5dbb4ec15b9ceb
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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