Triethylamine → 2-Cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine

HRID 928592Notes

Reaction equation

HRID 928592 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:24]1[C:25]2[C:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])=[CH:34][S:33][C:26]=2[N:27]=[C:28]([CH:30]2[CH2:32][CH2:31]2)[N:29]=1>C(O)C>[CH:30]1([C:28]2[N:29]=[C:24]([N:13]3[CH2:14][CH2:15][CH:10]([CH2:9][O:8][CH2:7][CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH2:11][CH2:12]3)[C:25]3[C:35]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[O:42][CH3:43])=[CH:34][S:33][C:26]=3[N:27]=2)[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineHCID 895793654-Chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine

Product 1

HCID 895796182-Cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidineYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine (0.10 g, 0.47 mmol), triethylamine (0.089 mL, 0.63 mmol) and 4-chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine (0.10 g, 0.32 mmol) were combined and heated to 50° C. in ethanol (10 mL) overnight. The solvent was removed at reduced pressure. The residue was taken up in DCM (20 mL), washed with water (20 mL) and the organic dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of DCM to 90/10/1 DCM/MeOH/NH4OH to afford 2-cyclopropyl-5-(2-methoxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxymethyl)-1-piperidyl]thieno[2,3-d]pyrimidine (0.03 g). LCMS: purity 100%, RT=3.62 min, M+1=493.1

Workup

  1. customThe solvent was removed at reduced pressure
  2. washwashed with water (20 mL)
  3. dry with materialthe organic dried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customThe resulting residue was purified by flash chromatography
  6. washeluting with a gradient of DCM to 90/10/1 DCM/MeOH/NH4OH

Sources & evidence

ORD record
ord-29d286d192074e6e95baeb6e9661b0f7
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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