Triethylamine → HCID 86619270, compound

HRID 2403440Notes

Reaction equation

HRID 2403440 reaction equation
Cl.N1[CH2:7][CH2:6][CH:5](CN2CCCC2=O)[CH2:4][CH2:3]1.[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16].[Cl:22][C:23]1[N:24]=[C:25]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[C:26]2[S:31]C(C=O)=[CH:29][C:27]=2[N:28]=1.C(O[BH-](O[C:50](=[O:52])[CH3:51])OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl.C(O)(=O)C>[Cl:22][C:23]1[N:24]=[C:25]([N:34]2[CH2:35][CH2:36][O:37][CH2:38][CH2:39]2)[C:26]2[S:31][C:16]([CH2:15][N:17]3[CH2:20][CH2:21][CH:3]([CH2:4][CH:5]4[CH2:6][CH2:7][CH2:51][C:50]4=[O:52])[CH2:19][CH2:18]3)=[CH:29][C:27]=2[N:28]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 21241491111247-63-3HCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 86619270HCID 86619270, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-Piperidin-4-ylmethyl-pyrrolidin-2-one hydrochloride salt in anhydrous 1,2-dichloroethane was added triethylamine (47 μL), the reaction mixture was stirred at room temperature for 2 hours. 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (99 mg) and glacial acetic acid were added, the reaction mixture was stirred at room temperature for 4 hours. Sodium triacetoxyborohydride (96 mg) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with a 50/50 mixture of saturated sodium bicarbonate solution and brine, dried (MgSO4) and the solvents removed in vacuo to give a crude residue. This was purified using column chromatography to give 2-[1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-ylmethyl]-cyclopentanone (73 mg).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 4 hours
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. washwashed with a 50/50 mixture of saturated sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customto give a crude residue
  7. customThis was purified

Sources & evidence

ORD record
ord-2e2d3cc3f39b420aa46556d17e562364
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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