Triethylamine → HCID 15611195, compound

HRID 845116Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([CH2:9][NH2:10])[CH2:8][CH2:7]1.[CH:11]1[N:16]=[C:15](Cl)[C:14]2[N:18]=[CH:19][N:20]([C@@H:21]3[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]3[OH:29])[C:13]=2[N:12]=1.C(N(CC)CC)C>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1([CH2:9][NH:10][C:15]2[C:14]3[N:18]=[CH:19][N:20]([C:13]=3[N:12]=[CH:11][N:16]=2)[C@@H:21]2[O:25][C@H:24]([CH2:26][OH:27])[C@@H:23]([OH:28])[C@H:22]2[OH:29])[CH2:8][CH2:7]1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 930036-Chloropurine riboside

HCID 156111751-[1-(Thiophen-2-yl)cyclopropyl]methanamine

Product 1

HCID 15611195HCID 15611195, compound

Procedure

Reaction of the above amine (1.53 g, 10 mmol) with 6-chloropurine riboside (2.87 g, 10 mmol) and triethylamine (2.02 g, 20 mmol) as described in Example 1 gives, after a second crystallization from ethanol, N6((1-thien-2-ylcyclopropyl)methyl)adenosine (2.90 g, 71%) as a fluffy off-white solid m.p. 136°-138.5° C. Found: C, 53.78; H, 5.45; N, 17.28; S, 7.52%. C18H21N5O4S calculated requires: C, 53.60; H, 5.21; N, 17.37; S, 7.94%.

Workup

customgives
customafter a second crystallization from ethanol, N6((1-thien-2-ylcyclopropyl)methyl)adenosine (2.90 g, 71%) as a fluffy off-white solid m.p. 136°-138.5° C

Sources & evidence

ORD record: ord-289ed8545e0c4b1aaacc738be5e4c0a8
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04755594

Reaction notes

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