Sodium hydride → HCID 86618533, compound

HRID 2426538Notes

Reaction equation

HRID 2426538 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)[CH3:2].[H-].[Na+].[Cl:22][C:23]1[N:28]=[C:27]([NH:29][CH:30]([CH3:32])[CH3:31])[CH:26]=[C:25](Cl)[N:24]=1>CN(C=O)C>[Cl:22][C:23]1[N:24]=[C:25]([NH:14][CH:11]2[CH2:10][CH2:9][N:8]([CH2:7][C:6]3[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=3)[CH2:13][CH2:12]2)[CH:26]=[C:27]([NH:29][CH:30]([CH3:32])[CH3:31])[N:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 214332662,6-Dichloro-N-(propan-2-yl)pyrimidin-4-amineHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 86618533HCID 86618533, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (39.7 mg, 0.15 mmol, 1.2 equiv; intermediate A1) in dry DMF (1.5 mL) was added sodium hydride (6.6 mg, 0.15 mmol, 1.2 equiv; 55% free-flowing powder moistened with oil) and the reaction mixture stirred at rt under Ar. After 2 h, (2,6-dichloro-pyrimidin-4-yl)-isopropyl-amine (25.8 mg, 0.125 mmol, 1.0 equiv) was added and the mixture heated to 120° C. for 48 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 7.1 mg (13%) of the title compound. MS (ISP): 434.3 [M+H]+.

Workup

  1. temperaturethe mixture heated to 120° C. for 48 h
  2. customRemoval of the solvent
  3. customunder reduced pressure and purification by preparative HPLC on reversed phase
  4. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-79f8751a8f9749be96a9c1ebe27e7a50
Source dataset
uspto-grants-2011_06
Patent number
US07968568B2

Reaction notes

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