Sodium hydride → HCID 68782053, compound

HRID 2264397Notes

Reaction equation

HRID 2264397 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[C:23]1[N:24]=[CH:25][C:26]2[C:31]([CH3:33])([CH3:32])[O:30][C:29]([CH3:35])([CH3:34])[C:27]=2[N:28]=1>CN(C=O)C>[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[CH2:9][CH2:10][CH:11]([NH:14][C:23]2[N:24]=[CH:25][C:26]3[C:31]([CH3:33])([CH3:32])[O:30][C:29]([CH3:35])([CH3:34])[C:27]=3[N:28]=2)[CH2:12][CH2:13]1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×HCID 58972435HCID 58972435, compound

Product 1

HCID 68782053HCID 68782053, compoundYield 19.3%

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, 1.5 equiv; intermediate A1) in dry DMF (1.5 mL) was added sodium hydride (6.6 mg, 0.15 mmol, 1.5 equiv; 55% free-flowing powder moistened with oil) and the reaction mixture stirred at rt under Ar. After 2 h 2-chloro-5,5,7,7-tetramethyl-5,7-dihydro-furo[3,4-d]pyrimidine (15.5 mg, 0.10 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 8.5 mg (12%) of the title compound. MS (ISP): 441.5 [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-e220fecea6804d499cb6e5628c4d889f
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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