Triphenylphosphine → HCID 58416768, compound

HRID 2069071Notes

Reaction equation

HRID 2069071 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[N+:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](O)=[CH:15][CH:14]=1)([O-:12])=[O:11].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([O:9][CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 2004934-Pyrimidinemethanol, 2-amino-HCID 3438294-Nitro-1-naphtholHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 58416768HCID 58416768, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (2-aminopyrimidin-4-yl)methanol (69) (700 mg, 3.92 mmol), 4-nitronaphthol (2) (741 mg, 3.92 mmol) and PPh3 (1.23 g, 4.70 mmol) in THF (20 mL) under nitrogen at −50° C. was added DIAD (996 μL, 4.70 mmol) dropwise over 5 min. The mixture was allowed to warm to RT and stirred for 1 hr during which time a yellow precipitate formed. The suspension was stirred overnight and the volatiles were evaporated in vacuo. The residue was triturated from MeOH (50 mL) and the pale yellow solid collected by filtration and washed with diethyl ether (50 mL) to give the title compound (70) (1.10 g, 93%): m/z 297 (M+H)+ (ES+).

Workup

  1. customformed
  2. stirringThe suspension was stirred overnight
  3. customthe volatiles were evaporated in vacuo
  4. customThe residue was triturated from MeOH (50 mL)
  5. filtrationthe pale yellow solid collected by filtration
  6. washwashed with diethyl ether (50 mL)

Sources & evidence

ORD record
ord-76274f93ec7c41cd9682112c3fc9f1cf
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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