Triethylamine → (1S,2R,4R)-4-{[6-Chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl]amino}-2-(hydroxymethyl)cyclopentanol

HRID 552729Notes

Reaction equation

HRID 552729 reaction equation
[NH2:1][C@H:2]1[CH2:6][C@H:5]([OH:7])[C@@H:4]([CH2:8][OH:9])[CH2:3]1.[Cl:10][C:11]1[C:16]([CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21])=[C:15](Cl)[N:14]=[CH:13][N:12]=1.C(N(CC)CC)C>C(O)CCC>[Cl:10][C:11]1[N:12]=[CH:13][N:14]=[C:15]([NH:1][C@H:2]2[CH2:6][C@H:5]([OH:7])[C@@H:4]([CH2:8][OH:9])[CH2:3]2)[C:16]=1[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10975515(1S,2R,4R)-4-amino-2-(hydroxymethyl)cyclopentanolHCID 197943054,6-Dichloro-5-(2,2-diethoxyethyl)pyrimidine

Product 1

HCID 86607318(1S,2R,4R)-4-{[6-Chloro-5-(2,2-diethoxyethyl)pyrimidin-4-yl]amino}-2-(hydroxymethyl)cyclopentanolYield 85.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (1S,2R,4R)-4-amino-2-(hydroxymethyl)cyclopentanol (0.485 g, 3.69 mmol) (Ho, J. Z.; Mohareb, R. M.; Anh, J. H.; Sim, T. B.; Rapoport, H. J. Org. Chem. 2003, 68, 109-114), 4,6-dichloro-5-(2,2-diethoxyethyl)pyrimidine (0.392 g, 1.48 mmol) (Montgomery, J. A.; Hewson, K. J. Med. Chem. 1967, 10, 665-667) and triethylamine (0.30 mL, 2.22 mmol) in butanol (4 mL) was microwave irradiated at 150° C. for 450 seconds. The solution was concentrated and purified by flash chromatography (100% EtOAc) to give the title compound (0.454 g, 85%).

Workup

  1. concentrationThe solution was concentrated
  2. custompurified by flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-e1f55c2b8f7d467ca6a40ac89ab76763
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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