Triphenylphosphine → HCID 10202622, compound

HRID 2181624Notes

Reaction equation

HRID 2181624 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[NH:14][C:13]=2[C:12](=[O:20])[N:11]([CH3:21])[CH2:10]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:41][O:42][CH2:43][CH:44](O)[CH2:45][CH2:46][CH3:47].CCOC(/N=N/C(OCC)=O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:17]2[N:16]=[C:15]([CH2:18][CH3:19])[N:14]([CH:44]([CH2:43][O:42][CH3:41])[CH2:45][CH2:46][CH3:47])[C:13]=2[C:12](=[O:20])[N:11]([CH3:21])[CH2:10]1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5462977Diethyl azodicarboxylateHCID 11278790HCID 11278790, compoundHCID 224818471-Methoxypentan-2-ol

Product 1

HCID 10202622HCID 10202622, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one (80 mg, 0.246 mmol) in anhydrous THF (1.2 mL) was heated to 50° C. PPh3 (100 mg, 0.492 mmol) and 1-methoxy-2-pentanol (87 mg, 0.738 mmol) were added. After stirring 5 min, DEAD (85 μL, 0.541 mmol) was added rapidly via syringe and the reaction mixture was stirred 25 min at 50° C. The mixture was cooled to rt and was poured into a separatory funnel containing saturated aqueous NaHCO3 (15 mL). The aqueous layer was extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. Purification of the residue by prep plates (1000 μM silica gel plates, 50% ethyl acetate/50% hexanes) followed by further purification by reverse phase HPLC furnished the title compound (59 mg, 56% yield) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.45 (d, J=2.2 Hz, 1H), 7.18 (dd, J=8.5, 2.2 Hz, 1H), 7.07 (d, J=8.4 Hz, 1H), 4.84 (ABq, J=11.4, Δυ=46.9 Hz, 2H), 4.24-4.17 (m, 2H), 3.79-3.74 (m, 1H), 3.32 (s, 3H), 2.96 (s, 3H), 2.75 (q, J=7.7 Hz, 2H), 2.21-2.05 (m, 1H), 1.95-1.81 (m, 1H), 1.30-1.20 (m, 5H), 0.92 (t, J=7.0 Hz, 3H); HRMS (ESI) m/e 425.1519 [(M+H)+, calcd for C20H26N15OCl2 425.1511].

Workup

  1. stirringthe reaction mixture was stirred 25 min at 50° C
  2. additionwas poured into a separatory funnel
  3. extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue by prep plates (1000 μM silica gel plates, 50% ethyl acetate/50% hexanes)
  9. customfollowed by further purification by reverse phase

Sources & evidence

ORD record
ord-da5b0c13a8ad474395529c3f11ee5d5f
Source dataset
uspto-grants-2005_05
Patent number
US06894045B2

Reaction notes

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