Tetrahydrofuran → HCID 10302554, compound

HRID 1060543Notes

Reaction equation

HRID 1060543 reaction equation
[CH:1]1([NH:7][C:8]2[N:16]=[C:15](I)[N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[C@@H:18]2[O:22][C@H:21]([C:23]([NH:25][CH2:26][CH3:27])=[O:24])[C@@H:20]([OH:28])[C@H:19]2[OH:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:30]1([CH2:36][CH2:37][NH2:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[C]=O.C1C[O:44][CH2:43]C1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:1]1([NH:7][C:8]2[N:16]=[C:15]([C:43]([NH:38][CH2:37][CH2:36][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:44])[N:14]=[C:13]3[C:9]=2[N:10]=[CH:11][N:12]3[C@H:18]2[C@H:19]([OH:29])[C@H:20]([OH:28])[C@@H:21]([C:23]([NH:25][CH2:26][CH3:27])=[O:24])[O:22]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 33944N-(2-Aminoethyl)piperidineHCID 10207977HCID 10207977, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 10302554HCID 10302554, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of (2S,3S,4R,5R)-5-[6-(cyclohexylamino)-2-iodo-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (Preparation 31) (125 mg, 0.24 mmol), 2-(1-piperidinyl)ethylamine (0.14 ml, 0.96 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.024 mmol) in THF (5 ml) was carbonylated at 60° C. and 345 KPa carbon monoxide for 18 hours. Solvent was evaporated under reduced pressure and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (95:5:1, by volume). After evaporation of appropriate fractions the residue was triturated with diethyl ether, filtered and dried to yield the target compound as a beige powder, (77 mg, 58%).

Workup

  1. customwas carbonylated at 60° C.
  2. customSolvent was evaporated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel eluting with dichloromethane
  4. customAfter evaporation of appropriate fractions the residue
  5. customwas triturated with diethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-6863c3ebb05d4bbb9770d321c704612f
Source dataset
uspto-grants-2003_02
Patent number
US06525032B2

Reaction notes

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