N-Hydroxyphthalimide → 4-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-phthalimidooxyethyl)-7h-pyrrolo[2,3-d]pyrimidine

HRID 915867Notes

Reaction equation

HRID 915867 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH2:11][CH2:12][OH:13])=[CH:9][N:8]([C@@H:14]3[O:29][C@H:28]([CH2:30][O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=4[Cl:40])[C@@H:17]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])[C@@:15]3([CH3:41])[OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:62]1[C:66](=[O:67])[C:65]2=[CH:68][CH:69]=[CH:70][CH:71]=[C:64]2[C:63]1=[O:72].CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O.C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([CH2:11][CH2:12][O:13][N:62]3[C:63](=[O:72])[C:64]4=[CH:71][CH:70]=[CH:69][CH:68]=[C:65]4[C:66]3=[O:67])=[CH:9][N:8]([C@@H:14]3[O:29][C@H:28]([CH2:30][O:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=4[Cl:40])[C@@H:17]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=4[Cl:27])[C@@:15]3([CH3:41])[OH:16])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

8

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 875057074-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-hydroxyethyl)-7h-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 875059054-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-phthalimidooxyethyl)-7h-pyrrolo[2,3-d]pyrimidineYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound 2.6 (359.0 mg, 0.54 mmol) in THF (10 mL) were added triphenylphosphine (215.0 mg, 0.82 mmol) and N-hydroxyphthalimide (132.0 mg, 0.0.81 mmol) followed by diethylazodicarboxylate (DEAD) (153 μL, 0.88 mmol), and the solution was stirred overnight at room temperature. The reaction mixture was diluted by adding 10 mL of CH2Cl2 and 10 mL of water. The aqueous layer was extracted three times with CH2Cl2, dried over Na2SO4, filtered and evaporated. The product was purified by flash column chromatography using 15-20% EtOAc in hexanes as eluent gave the desired compound 2.7 (369 mg, 85%) as a white solid.

Workup

  1. additionThe reaction mixture was diluted
  2. extractionThe aqueous layer was extracted three times with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was purified by flash column chromatography

Sources & evidence

ORD record
ord-b3800ed94b9d447db4d2e389e6a4f279
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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