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Diisopropylamine → 2-(6-Cyano-1-hexyn-1-yl)adenosine

HRID 719085
Notes
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Reaction equation

HRID 719085 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].C(NC(C)C)(C)C.[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35])#[N:29]>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[C:35][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])#[N:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 1696622-IodoadenosineHCID 117685266-Heptynenitrile

Product 1

HCID 112109712-(6-Cyano-1-hexyn-1-yl)adenosineYield 55%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

Under argon, to a solution of 2-iodoadenosine (420 mg, 1.07 mmol) and bis(triphenylphosphine)palladium dichloride (75 mg, 10 mol %) dissolved in N,N-dimethylformamide (10 mL), diisopropylamine (0.18 mL, 1.28 mmol, 1.2 eq.) and 6-cyano-1-hexyne (137 mg, 1.28 mmol, 1.2 eq.) were added, and, under ice-cooling conditions, cuprous iodide (10 mg, 5 mol %) was added thereto, followed by stirring at 50° C. for 24 hours. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was purified by dry packed silica gel column chromatography (ethyl acetate:methanol=10:1), to thereby yield a compound of the present invention as a pale yellow powder (yield: 217 mg, percent yield: 55%).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified
  5. customby dry
  6. customto thereby yield a compound of the present invention as a pale yellow powder (yield: 217 mg, percent yield: 55%)

Sources & evidence

ORD record
ord-fe9b2120a8cd4a878c4844adcc2be5b0
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07132409B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes