9-{2-[2-(3-Azidomethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-3-nitro-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one → HCID 11202501, compound

HRID 1785423Notes

Reaction equation

HRID 1785423 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH2:11][CH:12]([NH:14][C:15]2[N:20]=[C:19]([N:21]3[C:26]4=[N:27][C:28]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[C:29]([N+:32]([O-])=O)[C:30](=[O:31])[N:25]4[CH2:24][CH2:23][CH2:22]3)[CH:18]=[CH:17][N:16]=2)[CH3:13])[CH:8]=[CH:9][CH:10]=1)=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:32][C:29]1[C:30](=[O:31])[N:25]2[CH2:24][CH2:23][CH2:22][N:21]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([NH:14][CH:12]([CH3:13])[CH2:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][NH2:1])[CH:6]=4)[N:20]=3)[C:26]2=[N:27][C:28]=1[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 866003739-{2-[2-(3-Azidomethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-3-nitro-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 11202501HCID 11202501, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9-{2-[2-(3-azidomethyl-phenyl) -1-methyl-ethylamino]-pyrimidin-4-yl}-3-nitro-2-phenyl-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (61 mg, 0.11 mmol) in 1 mL methanol was safely added 10 mg palladium on carbon (10%) and stirred over an atmosphere of hydrogen delivered by a balloon. After 2 h, the reaction was filtered through a bed of Celite and solvent removed under reduced pressure. Product was purified on silica. M+1=483 1H NMR (CDCl3) d (3H, 1.19 ppm), m (2H, 2.20 ppm), dd (1H, 2.76 ppm), dd (1H, 2.96 ppm), s (2H, 3.84 ppm), m (6H, 4.08 ppm), q (1H, 4.30 ppm), d (1H, 4.95 ppm), m (4H, 7.13 ppm), t (1H, 7.28 ppm), t (1H, 7.36 ppm), t (2H, 7.45 ppm), d (2H, 7.80 ppm), d (1H), 8.03 ppm).

Workup

  1. filtrationthe reaction was filtered through a bed of Celite and solvent
  2. customremoved under reduced pressure
  3. customProduct was purified on silica

Sources & evidence

ORD record
ord-9476fd4ddc2340ed84f7afe148dc3f1e
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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