3,3-Dimethylbutanal → HCID 117839512, compound

HRID 1477702Notes

Reaction equation

HRID 1477702 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:9][C:8]2=[O:19])=[CH:4][CH:3]=1.[CH3:22][C:23]([CH3:28])([CH3:27])[CH2:24][CH:25]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:25][CH2:24][C:23]([CH3:28])([CH3:27])[CH3:22])[CH2:15][CH2:14]3)=[N:9][C:8]2=[O:19])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate waterHCID 117839396HCID 117839396, compound

Product 1

HCID 117839512HCID 117839512, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a dichloromethane solution (1 mL) of 1-(4-chlorobenzyl)-4-(piperazin-1-yl)-1,3,5-triazin-2(1H)-one (31 mg, 0.10 mmol) synthesized in Reference Synthesis Example 9 and 3,3-dimethylbutanal (13 μL, 0.10 mmol), sodium triacetoxyborohydride (42 mg, 0.20 mmol) was added and the resultant mixture was stirred at room temperature for 4 hours. After the completion of the reaction, saturated sodium bicarbonate water was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed. The organic layer was concentrated under reduced pressure and to the resultant residue, ethyl acetate was added. A resultant solid was filtered and was dried under reduced pressure to obtain the title compound (11 mg, yield: 28%).

Workup

  1. additionwas added
  2. customreaction solution
  3. concentrationThe organic layer was concentrated under reduced pressure and to the resultant residue, ethyl acetate
  4. additionwas added
  5. filtrationA resultant solid was filtered
  6. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-e70bea16713e410b8e8df449ea2780f4
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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