Ethylenediamine → HCID 131724463, compound

HRID 353627Notes

Reaction equation

HRID 353627 reaction equation
C[C:2]1[N:3]([C@H:30]2[C@H:34]([OH:35])[C@H:33]([OH:36])[C@@H:32]([CH2:37][OH:38])[O:31]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:7]=[C:6]([CH2:26][C:27]([NH2:29])=[O:28])[N:5]=2.[CH2:39](N)[CH2:40][NH2:41]>ClCCl>[NH2:41][CH2:40][CH2:39][NH:29][C:27]([CH2:26][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[CH:2][N:3]2[C@H:30]2[C@H:34]([OH:35])[C@H:33]([OH:36])[C@@H:32]([CH2:37][OH:38])[O:31]2)=[C:8]([NH:11][CH2:12][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:7]=1)=[O:28]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 131724464HCID 131724464, compound

Product 1

HCID 131724463HCID 131724463, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of methyl 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxyamide (Preparation 16) (0.52 g, 1.03 mmol) and 1,2-ethylenediamine (0.6 g, 10 mmol) was heated at 105° C. for 3 hours. The mixture was dissolved in a little dichloromethane and purified by column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (85:15:1.5, by volume). After evaporation of appropriate fractions the residue was triturated with diethyl ether, filtered and dried to yield the target compound as a white solid, (0.43 g, 78%).

Workup

  1. custompurified by column chromatography on silica gel eluting with dichloromethane
  2. customAfter evaporation of appropriate fractions the residue
  3. customwas triturated with diethyl ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-78875c5b83164843a0d44dd8404cdea8
Source dataset
uspto-grants-2004_06
Patent number
US06753322B2

Reaction notes

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