2-Naphthalenecarboxaldehyde → HCID 49855398, compound

HRID 2079811Notes

Reaction equation

HRID 2079811 reaction equation
[NH2:1][CH2:2][CH:3]1[CH:8]2[CH:4]1[CH2:5][N:6]([C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=1)[CH2:7]2.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH:30]=O.[BH4-].[Na+].[NH4+].[Cl-]>CO.O>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH2:30][NH:1][CH2:2][CH:3]1[CH:8]2[CH:4]1[CH2:5][N:6]([C:9]1[N:10]=[CH:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1)[CH2:7]2

Participants

7

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 49857516Ethyl 2-[6-(aminomethyl)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxylate

Product 1

HCID 49855398HCID 49855398, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-[6-(aminomethyl)-3-azabicyclo[3.1.0]hex-3-yl]pyrimidine-5-carboxylate (200 mg, 0.76 mmol) was stirred with 2-naphthaldehyde (119 mg, 0.76 mmol) in MeOH (10 ml) at r.t. under N2 for 16 h. NaBH4 (46 mg, 1.22 mmol) was then added and the mixture stirred for 10 min. Sat. aq. NH4Cl (20 ml) was added and the mixture stirred for 20 min. The reaction was then diluted with H2O (50 ml) and extracted with Et2O (2×100 ml). The combined organic layers were dried (MgSO4) and the solvent removed in vacuo to give the title compound as a yellow oil which was used in the next step without further purification. LCMS purity 92%, m/z 403 [M+H]+.

Workup

  1. stirringthe mixture stirred for 20 min
  2. extractionextracted with Et2O (2×100 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8de67212087f4628bed91103e0b3d2c3
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

Loading…