Diisopropylethylamine → HCID 68851187, compound

HRID 2108342Notes

Reaction equation

HRID 2108342 reaction equation
[NH:1]([C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13]2)=[C:5]([NH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)[N:4]=1)[NH2:2].[CH:27]([CH:29]([CH:35]=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=O.C(N(C(C)C)CC)(C)C>C(O)C>[OH:17][C@@H:16]1[C@H:15]([OH:18])[C@@H:14]([CH2:19][OH:20])[O:13][CH:12]1[N:9]1[CH:8]=[N:7][C:6]2[C:10]1=[N:11][C:3]([N:1]1[CH:35]=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:2]1)=[N:4][C:5]=2[NH:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11029955Ethyl 2-formyl-3-oxopropanoateHCID 59729898HCID 59729898, compound

Product 1

HCID 68851187HCID 68851187, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4S,2R,3R,5R)-2-[2-hydrazino-6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol (0.2 mmol) and ethyl 2,2-diformylacetate (0.28 mmol) were suspended in 3 mL of ethanol and to the suspension was added 5 mmol of diisopropylethylamine. The mixture was heated at reflux for 3 hours. Upon cooling to room temperature, the precipitate thus formed was collected by filtration, and washed with ethanol and ether to afford ethyl 1-{9-[(4S,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(cyclopentylamino)purin-2-yl}pyrazole-4-carboxylate, a compound of Formula I.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customthe precipitate thus formed
  4. filtrationwas collected by filtration
  5. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-770c50fed65d467aa501b413bd9c8f16
Source dataset
uspto-grants-2009_04
Patent number
US07514417B2

Reaction notes

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