Diisopropylethylamine → HCID 58504473, compound

HRID 2367598Notes

Reaction equation

HRID 2367598 reaction equation
[CH3:1][C@H:2]1[O:7][CH2:6][C@@H:5]([CH3:8])[NH:4][CH2:3]1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[C:12]([NH:17][CH3:18])[N:11]=1.CCN(C(C)C)C(C)C>CC#N>[Cl:9][C:10]1[CH:15]=[C:14]([N:4]2[C@H:5]([CH3:8])[CH2:6][O:7][C@H:2]([CH3:1])[CH2:3]2)[N:13]=[C:12]([NH:17][CH3:18])[N:11]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2598804,6-Dichloro-n-methylpyrimidin-2-amineHCID 28819207(2R,5R)-2,5-Dimethylmorpholine

Product 1

HCID 58504473HCID 58504473, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2R,5R)-2,5-dimethylmorpholine (400 mg, 3.47 mmol) and 4,6-dichloro-N-methyl-2-pyrimidinamine (742 mg, 4.17 mmol) in CH3CN (5 mL) stirred at room temperature was added Hunig's base (1.213 mL, 6.95 mmol). The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 120° C. for 1 hour. After cooling the reaction, the mixture was concentrated under reduced pressure and the residue was added to a silica gel column and was eluted with Hex/EtOAc (10:1 to 3:1). Collected fractions:the first fraction was the starting material 4,6-dichloro-N-methyl-2-pyrimidinamine (300 mg), and the second fraction was the title compound (460 mg) as a light yellow solid. LC-MS (ES) m/z=257 [M+H]+.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in Biotage Initiator
  3. customnormal to 120° C.
  4. customfor 1 hour
  5. temperatureAfter cooling
  6. customthe reaction
  7. concentrationthe mixture was concentrated under reduced pressure
  8. additionthe residue was added to a silica gel column
  9. washwas eluted with Hex/EtOAc (10:1 to 3:1)

Sources & evidence

ORD record
ord-f90f2aad4bc14a65a21ec397bf1e8ec5
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…