Sodium triacetoxyborohydride → 5-{4-[2-(4-Diethylamino-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1-ethyl-1H-pyrimidine-2,4-dione

HRID 642871Notes

Reaction equation

HRID 642871 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)[CH3:2].[CH2:27]([N:29]1[CH:34]=[C:33]([CH:35]=O)[C:32](=[O:37])[NH:31][C:30]1=[O:38])[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.O>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([N:19]4[CH2:20][CH2:21][N:22]([CH2:35][C:33]5[C:32](=[O:37])[NH:31][C:30](=[O:38])[N:29]([CH2:27][CH3:28])[CH:34]=5)[CH2:23][CH2:24]4)[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)[CH3:26]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 576783031-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehydeHCID 58592734Diethyl-[4-(4-piperazin-1-yl-1H-benzoimidazol-2-yl)-phenyl]-amine

Product 1

HCID 115696245-{4-[2-(4-Diethylamino-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1-ethyl-1H-pyrimidine-2,4-dioneYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of Diethyl-[4-(4-piperazin-1-yl-1H-benzoimidazol-2-yl)-phenyl]-amine (1.0 g, 2.0 mMol) in N-methylpyrrolidinone (10 mL) was added 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde (0.404 g, 2.40 mMol) followed by sodium triacetoxyborohydride (0.849 g, 4.01 mMol) and the mixture stirred at room temperature overnight. Upon arrival the crude reaction mixture was diluted with water (2 mL), filtered, and purified by RP-HPLC (Method E) to yield 168 mg (17% yield) of 5-{4-[2-(4-Diethylamino-phenyl)-1H-benzoimidazol-4-yl]-piperazin-1-ylmethyl}-1-ethyl-1H-pyrimidine-2,4-dione as a very light yellow solid. 1H NMR (DMSO-d6): δ=12.33 (s,1H), 11.25 (s,1H), 7.91 (d, 2H, J=9 Hz), 7.66 (s, 1H), 6.96 (m, 2H), 6.77 (d,2H, J=9 Hz), 6.45 (dd, 1H, J=6.0, 2.8 Hz), 3.74 (q, 2H, J=7.1 Hz), 3.53 (br s, 4 h), 3.40 (q, 4H, J=7.1 Hz), 3.23 (s, 2H), 2.62 (m, 4H), 1.18 (t, 3H, J=7.1 Hz), 1.13 (t, 6H, J=7.1 Hz). LC/MS (Method A), rt=0.85 mins., purity=99.2%, calculated mass=501, [M+H]+=502, [M−H]=500. HPLC (Method D): rt=5.5 mins., purity=99.3% @ 210-370 nm and 98.6% @ 372 nm.

Workup

  1. customUpon arrival the crude reaction mixture
  2. filtrationfiltered
  3. custompurified by RP-HPLC (Method E)

Sources & evidence

ORD record
ord-a6e894c1d0254f52adc7a3b44c689412
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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