Ethylenediamine → HCID 67022995, compound

HRID 215887Notes

Reaction equation

CO[C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([NH:19][C:20](=[O:26])[CH2:21][O:22]C(=O)C)[C@@H:16]([OH:27])[C@H:15]2[OH:28])=[C:7]([NH:29][C@H:30]([CH2:38][OH:39])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:6]=1)=[O:4].[CH2:40]([NH2:43])[CH2:41][NH2:42]>>[NH2:42][CH2:41][CH2:40][NH:43][C:3]([C:5]1[N:13]=[C:12]2[C:8]([N:9]=[CH:10][N:11]2[C@@H:14]2[CH2:18][C@H:17]([NH:19][C:20](=[O:26])[CH2:21][OH:22])[C@@H:16]([OH:27])[C@H:15]2[OH:28])=[C:7]([NH:29][C@H:30]([CH2:38][OH:39])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:6]=1)=[O:4]

Participants

Reactant 2

HCID 3301Ethylenediamine

HCID 67022994HCID 67022994, compound

Product 1

HCID 67022995HCID 67022995, compound

Conditions

Temperature: 90 °C

Procedure

9-[(1R,2S,3R,4S)-4-(2-Acetoxy-acetylamino)-2,3-dihydroxy-cyclopentyl]-6-((S)-1-hydroxymethyl-2-phenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester (Intermediate WF) is dissolved in ethylenediamine (>10 eq.). The reaction mixture is stirred at 90° C. for 1 hour. The reaction mixture is cooled and reduced in vacuo. The title compound is obtained by column chromatography.

Workup

temperatureThe reaction mixture is cooled

Sources & evidence

ORD record: ord-4a85a282aabd42689d22624cf7871852
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193164B2

Reaction notes

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