6-Chloropurine riboside → HCID 15611201, compound

HRID 845122Notes

Reaction equation

HRID 845122 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([CH2:10][NH2:11])[CH2:9][CH2:8][CH2:7]1.[CH:12]1[N:17]=[C:16](Cl)[C:15]2[N:19]=[CH:20][N:21]([C@@H:22]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@H:23]3[OH:30])[C:14]=2[N:13]=1>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([CH2:10][NH:11][C:16]2[C:15]3[N:19]=[CH:20][N:21]([C:14]=3[N:13]=[CH:12][N:17]=2)[C@@H:22]2[O:26][C@H:25]([CH2:27][OH:28])[C@@H:24]([OH:29])[C@H:23]2[OH:30])[CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 930036-Chloropurine ribosideHCID 15611178HCID 15611178, compound

Product 1

HCID 15611201HCID 15611201, compoundYield 76.2%

Procedure

The above amine (1.67 g, 10 mmol) is reacted with 6-chloropurine riboside (2.87 g, 10 mmol) as described in Example 1 and 7 is purified by column chromatography to give N6-(1-(thien-2-ylcyclobutyl)methyl)adenosine (3.18 g, 76%) as a colorless glass m.p. 84°-92° C. Found: C, 54.88; H, 5.69; N, 16.77; S, 7.55%. C19H23N5O4S calculated requires: C, 54.68; H, 5.52; N, 16.79; S, 7.67%.

Workup

  1. customis purified by column chromatography

Sources & evidence

ORD record
ord-feaa653c08e14518aacb5aed2edc546b
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

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