Triphenylphosphine → 2-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one

HRID 2055663Notes

Reaction equation

HRID 2055663 reaction equation
[N:1]([CH:4]([C:8]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:25])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][N:14]=2)[N:9]=1)[CH:5]([CH3:7])[CH3:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][CH:4]([C:8]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:16](=[O:25])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][N:14]=2)[N:9]=1)[CH:5]([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 22172628HCID 22172628, compound

Product 1

HCID 221726212-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-oneYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Formula 107 where R2 and R3 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; X and Y are —C═; and W and Z are —N═: To a solution of THF (100 mL), 2-(1-azido-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one (3.75 mmol) and triphenylphosphine (0.984 g, 3.75 mmol) was added 2N HCL (15 mL). The reaction mixture was stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The residue was purified by flash silica gel chromatography using EtOAc-MeOH (50:1 to 10:1) as eluent to give the desired amino product of Formula 107, 2-(1-amino-2-methyl-propyl)-3-benzyl-3H-pteridin-4-one (0.880 g, 76% from Formula 105). MS (Cl) M/E: 310.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-b0a9ed74f84a44eab01452203c6cc644
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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