Triethylamine → (1R,2S,3R,5R)-3-((6-chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

HRID 511596Notes

Reaction equation

HRID 511596 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:6]([Cl:16])[N:5]=[CH:4][N:3]=1.[Cl-].[OH:18][C@@H:19]1[C@H:23]([OH:24])[C@@H:22]([CH2:25][OH:26])[CH2:21][C@H:20]1[NH3+:27].CCN(CC)CC>C(O)C>[Cl:16][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:27][C@@H:20]2[CH2:21][C@H:22]([CH2:25][OH:26])[C@@H:23]([OH:24])[C@H:19]2[OH:18])[C:7]=1[CH2:8][CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 197943054,6-Dichloro-5-(2,2-diethoxyethyl)pyrimidineHCID 178479579HCID 178479579, compound

Product 1

HCID 86666111(1R,2S,3R,5R)-3-((6-chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl)amino)-5-(hydroxymethyl)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloro-5-(2,2-diethoxyethyl)pyrimidine (5.35 g, 20.2 mmol) and (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentanaminium chloride (9.29 g, 24.3 mmol) was taken up in ethanol (236 mL), treated with Et3N (11.2 mL, 80.8 mmol) and heated at reflux for 23 h; HPLC/LC MS indicated consumption of starting materials and presence of product. The reaction mixture was concentrated to afford a tan slurry, which was carried on crude: MS (ESI+) for C16H26ClN3O5 m/z 376.2 (M+H)+; MS (ESI−) for C16H26ClN3O5 m/z 374.2 (M−H)−; HPLC purity >95% (ret. time, 2.436 min). Variation on route from J. Med. Chem. 10, 665 (1967).

Workup

  1. temperatureheated
  2. temperatureat reflux for 23 h
  3. customconsumption of starting materials and presence of product
  4. concentrationThe reaction mixture was concentrated
  5. customto afford a tan slurry, which
  6. customHPLC purity >95% (ret. time, 2.436 min)

Sources & evidence

ORD record
ord-33bc89be990a47ebb9534c01f341ff88
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

Loading…