Triphenylphosphine → HCID 59395803, compound

HRID 1097634

Reaction equation

HRID 1097634 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([Cl:15])[N:11]([CH2:16][CH:17]=[CH2:18])[C:10]=2[C:9](=[O:19])[NH:8][C:7]1=[O:20])[CH2:2][CH2:3][CH2:4][CH3:5].[NH:21]1[CH:25]=[C:24]([CH2:26][CH2:27][CH2:28]O)[CH:23]=[N:22]1.N(C(OCC1C=CC=CC=1)=O)=NC(OCC1C=CC=CC=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[Cl:15][C:12]1[N:11]([CH2:16][CH:17]=[CH2:18])[C:10]2[C:9](=[O:19])[N:8]([CH2:28][CH2:27][CH2:26][C:24]3[CH:25]=[N:21][NH:22][CH:23]=3)[C:7](=[O:20])[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]=2[N:13]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 35783843-(1H-pyrazol-4-yl)propan-1-olHCID 59299557HCID 59299557, compound

Product 1

HCID 59395803HCID 59395803, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Pentyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (5 g, 16.86 mmol) and 3-(1H-pyrazol-4-yl)propan-1-ol (2.12 g, 16.8 mmol) were stirred in dry THF (150 ml) at 3° C. Dibenzyl azodicarboxylate (10.05 g, 33.7 mmol) was added followed by the dropwise addition of triphenylphosphine (8.83 g, 33.7 mmol) in dry THF (70 ml). The mixture was allowed to warm to it and stirred for 18 h. Water (1 ml) was added and the solvents evaporated. The residue was taken up in Et2O (200 ml) from which a white solid, mostly triphenylphosphine oxide, crystallised and was filtered off. The filtrate was concentrated and further by-products crystallised from ether-cyclohexane. The remaining filtrate was concentrated (19.2 g) and purified on a Biotage™ system (400 g) eluting with EtOAc-cyclohexane (2:1) to afford the title compound as a white solid (2.89 g).

Workup

  1. temperatureto warm to it
  2. customthe solvents evaporated
  3. customcrystallised
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated
  6. customfurther by-products crystallised from ether-cyclohexane
  7. concentrationThe remaining filtrate was concentrated (19.2 g)
  8. custompurified on a Biotage™ system (400 g)
  9. washeluting with EtOAc-cyclohexane (2:1)

Sources & evidence

ORD record
ord-a351c52f866a4ef3827555a2cc86e10d
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Linked notes

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