2-Amino-4-chloro-6-methylpyrimidine → HCID 86640062, compound

HRID 2242954Notes

Reaction equation

HRID 2242954 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[CH2:10]([O:12][C:13]1[CH:14]=[C:15]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)[CH3:11]>CC(N(C)C)=O>[CH2:10]([O:12][C:13]1[CH:14]=[C:15]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([NH:23][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[N:3]=2)[CH2:21][CH2:22]1)[CH3:11]

Participants

4

Reactant 2

HCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 86640062HCID 86640062, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 4-chloro-6-methyl-pyrimidin-2-ylamine (21.5 mg, 0.15 mmol, 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in DMAc (2 mL) was heated by microwave irradiation to 180° C. for 40 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 6.1 mg (11%) of the title compound. MS (ISP): 372.3 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-c7fdb74901c742648c3bc1b76799d2a5
Source dataset
uspto-grants-2010_03
Patent number
US07674804B2

Reaction notes

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