Diisopropylethylamine → 6-Bromo-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928563Notes

Reaction equation

HRID 928563 reaction equation
[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.[N:27]1([CH2:32][CH2:33][O:34][CH2:35][CH:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:31][CH2:30][CH2:29][CH2:28]1>C1COCC1.O>[Br:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([N:39]3[CH2:40][CH2:41][CH:36]([CH2:35][O:34][CH2:33][CH2:32][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:37][CH2:38]3)[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 895795126-Bromo-4-chloro-5-phenyl-thieno[2,3-d]pyrimidine

Product 1

HCID 1177396476-Bromo-5-phenyl-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidineYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-bromo-4-chloro-5-phenyl-thieno[2,3-d]pyrimidine (0.820 g, 2.52 mmol) in THF (50 mL), was added diisopropylethylamine (0.65 mL, 3.78 mmol) and 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (0.801 g, 3.78 mmol) in one portion, and the reaction left to stir at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The reaction was dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography using DCM: MeOH (0-25%) as eluent to afford the named product (0.828 g, 66%).

Workup

  1. waitthe reaction left
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe reaction was dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-1b9d70a88e734316a49f3e73505b9873
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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