Pyrimidine, 2,4-dichloro-5-methyl- → HCID 86761063, compound

HRID 2242952Notes

Reaction equation

HRID 2242952 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH3:9])=[CH:4][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]>C(O)CO>[Cl:1][C:2]1[N:7]=[C:6]([NH:23][CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][C:15]3[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:13]([O:12][CH2:10][CH3:11])[CH:14]=3)[CH2:18][CH2:19]2)[C:5]([CH3:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 74508Pyrimidine, 2,4-dichloro-5-methyl-HCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 86761063HCID 86761063, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A solution of 2,4-dichloro-5-methyl-pyrimidine (16.3 mg, 0.10 mmol, 1.0 equiv; commercially available) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (39.7 mg, 0.15 mmol, 1.5 equiv; intermediate A1) in ethylene glycol (2 mL) was heated by microwave irradiation to 200° C. for 15 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 4.0 mg (7%) of the title compound. MS (ESI): 391.4 [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-e9fff7181cea46afad41d0135aa0279b
Source dataset
uspto-grants-2010_03
Patent number
US07674804B2

Reaction notes

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