2,4,6-Trimethylbenzaldehyde → HCID 58625150, compound

HRID 390222Notes

Reaction equation

HRID 390222 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[N:17]([CH2:18][CH2:19][CH3:20])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH2:29])[CH:23]=3)[CH:14]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][C:32]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[C:33]=1[CH:34]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[N:17]([CH2:18][CH2:19][CH3:20])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH2:34][C:33]4[C:36]([CH3:41])=[CH:37][C:38]([CH3:40])=[CH:39][C:32]=4[CH3:31])[CH:23]=3)[CH:14]=2)[N:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 102542,4,6-TrimethylbenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58625148HCID 58625148, compound

Product 1

HCID 58625150HCID 58625150, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under N2, a mixture of [6-(3-aminomethyl-phenoxy)-3-propyl-3,4-dihydro-quinazolin-2-yl]-carbamic acid tert-butyl ester (0.0007 mol) and 2,4,6-trimethyl-benzaldehyde (0.0007 mol) in DCE (10 mL) was stirred at room temperature, then NaBH(OAc)3 (0.2 g) was added, and the reaction mixture was stirred overnight at room temperature. A saturated NaHCO3 solution was added, and the layers were separated. The organic layer was dried, filtered off and the solvent was evaporated. The residue was purified by Biotage column chromatography (gradient eluent: CH2Cl2:CH3OH). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. filtrationfiltered off
  5. customthe solvent was evaporated
  6. customThe residue was purified by Biotage column chromatography (gradient eluent: CH2Cl2:CH3OH)
  7. customThe purest product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-04f2683a0d3e4a589684087bd8844ea5
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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