Diisopropylethylamine → (2S,4R)-5-Propyl-2-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine

HRID 431827Notes

Reaction equation

HRID 431827 reaction equation
[F:1][C:2]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:3]=1[CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][NH:8]1.Cl[C:39]1[N:44]=[CH:43][C:42]([CH2:45][CH2:46][CH3:47])=[CH:41][N:40]=1.C(N(C(C)C)C(C)C)C>[Cu]I>[CH2:45]([C:42]1[CH:41]=[N:40][C:39]([N:8]2[CH2:9][C@H:10]([S:12][C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:11][C@H:7]2[CH2:6][O:5][CH2:4][C:3]2[CH:32]=[C:33]([F:37])[C:34]([F:36])=[CH:35][C:2]=2[F:1])=[N:44][CH:43]=1)[CH2:46][CH3:47]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357842-Chloro-5-propylpyrimidineHCID 11398267(2S,4R)-2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine

Product 1

HCID 11342680(2S,4R)-5-Propyl-2-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidineYield 81.2%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of 2 g (3.85 mmol)(2S,4R)-2-(2,4,5-Trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidine, 1.2 g (7.7 mmol) 2-chloro5-n-propylpyrimidine, 1.98 ml (11.55 mmol) N-ethyldiisopropylamine and a catalytic amount of copper(I) iodide was heated for 10 h at 80° C. The reaction was cooled and partitioned between H2O/Et2O (3×300). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried (NaSO4) and evaporated. Flash chromatography on silica gel (toluene/Et2O 99:1) gave 2 g (81%) (2S,4R)-5-Propyl-2-[2-(2,4,5-trifluoro-benzyloxymethyl)-4-tritylsulfanyl-pyrrolidin-1-yl]-pyrimidine, MS: 640 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between H2O/Et2O (3×300)
  3. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  4. dry with materialdried (NaSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-4ef3d44b6cf14c7f816cbf2c720f1e06
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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