Diisopropylethylamine → 6-Chloro-2-methyl-N4-(tetrahydro-2H-pyran-4-yl)-4,5-pyrimidinediamine

HRID 888964Notes

Reaction equation

HRID 888964 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[NH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>CC(O)C.ClCCl>[Cl:9][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:7]=1[NH2:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Product 1

HCID 593745576-Chloro-2-methyl-N4-(tetrahydro-2H-pyran-4-yl)-4,5-pyrimidinediamine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

Heat a solution of 4,6-Dichloro-2-methyl-pyrimidin-5-ylamine (0.008 mol, 1.5 g, 1.0 equiv.), 4-amino tetrahydropyran (0.012 mol, 1.27 g, 1.5 equiv.), and N,N-diisopropylethylamine (0.0092 mol, 1.1 g, 1.1 equiv.) in 2-propanol (80 mL) at 150° C. in a sealed tube for 16 hours. Cool the reaction mixture to room temperature and remove the 2-propanol under reduced pressure to give the residue. Dissolve the residue in dichloromethane and wash with water and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue on silica gel column eluting with dichloromethane: methanol 96:4 to give the title compound. MS (m/z): 243.41 (M+1).

Workup

  1. customremove the 2-propanol under reduced pressure
  2. customto give the residue
  3. washwash with water and brine
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customPurify the residue on silica gel column
  9. washeluting with dichloromethane: methanol 96:4

Sources & evidence

ORD record
ord-8e54862c7ce44e13896312ca54ad10a4
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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