Acetic Acid → HCID 86619269, compound

HRID 2403436Notes

Reaction equation

HRID 2403436 reaction equation
Cl.[N:2]1([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[N:3]1.[Cl:14][C:15]1[N:16]=[C:17]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:18]2[S:23][C:22]([CH:24]=O)=[CH:21][C:19]=2[N:20]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl.C(N(CC)CC)C>[Cl:14][C:15]1[N:16]=[C:17]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[C:18]2[S:23][C:22]([CH2:24][N:11]3[CH2:10][CH2:9][CH:8]([CH2:7][N:2]4[CH:6]=[CH:5][CH:4]=[N:3]4)[CH2:13][CH2:12]3)=[CH:21][C:19]=2[N:20]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 66617726956034-62-1

Product 1

HCID 86619269HCID 86619269, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-Pyrazol-1-ylmethyl-piperidine hydrochloride salt in 1,2-dichloroethane (5 ml) was added 2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (230 mg) and glacial acetic acid (50 μL). The reaction mixture was stirred at room temperature for 6 hours. Sodium triacetoxyborohydride (224 mg) and triethylamine (113 μL) were 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 product. This was purified by flash chromatography to yield 2-Chloro-4-morpholin-4-yl-6-(4-pyrazol-1-ylmethyl-piperidin-1-ylmethyl)-thieno[3,2-d]pyrimidine (154 mg).

Workup

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

Sources & evidence

ORD record
ord-3b03ecdd829c43d5af636a13acac5430
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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