Triethylamine → N6-((1-(4-chlorophenyl)cyclopropyl)methyl)adenosine

HRID 845126

Reaction equation

HRID 845126 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][NH2:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:13]1[N:18]=[C:17](Cl)[C:16]2[N:20]=[CH:21][N:22]([C@@H:23]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]3[OH:31])[C:15]=2[N:14]=1.C(N(CC)CC)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:11][NH:12][C:17]3[C:16]4[N:20]=[CH:21][N:22]([C:15]=4[N:14]=[CH:13][N:18]=3)[C@@H:23]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:25]([OH:30])[C@H:24]3[OH:31])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 4120166[1-(4-Chlorophenyl)cyclopropyl]methanamine

Product 1

HCID 15611207N6-((1-(4-chlorophenyl)cyclopropyl)methyl)adenosineYield 47%

Procedure

Reaction of the above amine (1.48 g, 8 mmol) with 6-chloropurine riboside (2.09 g, 7.3 mmol) and triethylamine (1.1 mL, 8 mmol) as prepared in Example 1 and 7 gives N6-((1-(4-chlorophenyl)cyclopropyl)methyl)adenosine (1.47 g, 47%) as a cream colored solid m.p. 132°-8° C. Found: C, 56.16; H, 5.22; N, 15.54; Cl, 9.12%. C20H22N5O4Cl calculated requires: C, 55.62; H, 5.10; N, 16.22; Cl, 8.23%.

Workup

  1. customas prepared in Example 1 and 7

Sources & evidence

ORD record
ord-7d0f2a7c4a6d4e8d8d3b706975eaad3f
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Linked notes

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