Methanol → HCID 58625122, compound

HRID 390240Notes

Reaction equation

HRID 390240 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=O.[C:12]([O:16][C:17](=[O:40])[NH:18][C:19]1[N:28]([CH2:29][CH2:30][CH3:31])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=3)[CH:25]=2)[N:20]=1)([CH3:15])([CH3:14])[CH3:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CO>ClCCCl>[C:12]([O:16][C:17](=[O:40])[NH:18][C:19]1[N:28]([CH2:29][CH2:30][CH3:31])[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][CH2:4][C:3]4[C:2]([CH3:1])=[CH:9][C:8]([CH3:10])=[CH:7][C:6]=4[CH3:11])[CH:34]=3)[CH:25]=2)[N:20]=1)([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 102542,4,6-TrimethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 58625068HCID 58625068, compound

Product 1

HCID 58625122HCID 58625122, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2,4,6-Trimethyl-benzaldehyde (0.0005 mol) was added to a mixture of [6-(3-amino-phenoxy)-3-propyl-3,4-dihydro-quinazolin-2-yl]-carbamic acid tert-butyl ester (0.0005 mol) in DCE (3 mL) and the mixture was stirred for 5 min. at room temperature, and then NaBH(OAc)3 (0.0006 mol) was added and the reaction mixture was stirred overnight at room temperature. The excess NaBH(OAc)3 was decomposed with CH3OH, and the solvent was evaporated. The obtained residue was purified by Biotage column chromatography (eluent: 100% CH2Cl2). The purest product fractions were collected and then the solvent was evaporated and co-evaporated with toluene to yield the title compound as a residue.

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customthe solvent was evaporated
  3. customThe obtained residue was purified by Biotage column chromatography (eluent: 100% CH2Cl2)
  4. customThe purest product fractions were collected
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d479f5ceddf049f385d280cd74f2e22c
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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