Ethylenediamine → HCID 18345899, compound

HRID 353624Notes

Reaction equation

C[C:2]1[N:3]([C@H:29]2[C@H:33]([OH:34])[C@H:32]([OH:35])[C@@H:31]([C:36]([NH:38][CH2:39][CH3:40])=[O:37])[O:30]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]([C:26]([NH2:28])=[O:27])[N:5]=2.[CH2:41](N)[CH2:42][NH2:43]>ClCCl>[NH2:43][CH2:42][CH2:41][NH:28][C:26]([C:6]1[N:5]=[C:4]2[C:9]([N:10]=[CH:2][N:3]2[C@H:29]2[C@H:33]([OH:34])[C@@H:32]([OH:35])[C@@H:31]([C:36]([NH:38][CH2:39][CH3:40])=[O:37])[O:30]2)=[C:8]([NH:11][CH2:12][CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:7]=1)=[O:27]

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 9) (1.1 g, 2 mmol) and 1,2-ethylenediamine (1.1 g, 18.3 mmol) was heated at 105° C. for 2.5 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, (0.99 g, 86%)

Workup

custompurified by column chromatography on silica gel eluting with dichloromethane
customAfter evaporation of appropriate fractions the residue
customwas triturated with diethyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-c77b6d7881984ba7b14916a71c474642
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06753322B2

Reaction notes

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