Triethylamine → HCID 54285389, compound

HRID 905230Notes

Reaction equation

HRID 905230 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.[C:9]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:21]([CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:20][C@H:19]1Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[C:9]([O:17][C@@H:18]1[C@H:22]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:21]([CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:20][C@H:19]1[S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71403455-Chloro-2(1H)-pyrimidinethioneHCID 12806351HCID 12806351, compound

Product 1

HCID 54285389HCID 54285389, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloropyrimidine-2-thione (4.3 mmol), 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl chloride (4.3 mmol) and triethylamine (4.3 mmol) in dichloromethane (25 ml) was stirred together at room temperature for 4 h, the mixture evaporated and the residue triturated with water; the residue was the title compound; yield 28% 1H NMR (CDCl3): δ4.75 (CH2), 6.0-6.5 (4 H), 7.2-8.2 (3 Ph), 8.50 (H-4, H-6).

Workup

  1. customthe mixture evaporated
  2. customthe residue triturated with water

Sources & evidence

ORD record
ord-e0e7c21d60a344e585aea957c10bfcc6
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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