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Triethylamine → HCID 178482373, compound

HRID 1801562
Notes
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Reaction equation

HRID 1801562 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[N:11]=[C:10]([OH:20])[CH:9]=2)[CH2:4][CH2:3]1.[CH3:21][NH:22][C:23]1[N:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][N:24]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[CH3:21][NH:22][C:23]1[N:28]=[CH:27][C:26]([CH2:29][N:2]2[CH2:7][CH2:6][CH:5]([C:8]3[N:13]=[C:12]([N:14]4[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]4)[N:11]=[C:10]([OH:20])[CH:9]=3)[CH2:4][CH2:3]2)=[CH:25][N:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31609752-(Methylamino)pyrimidine-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178479621HCID 178479621, compound

Product 1

HCID 178482373HCID 178482373, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-piperidin-4-yl-2-piperidin-1-yl-pyrimidin-4-ol, hydrochloride salt (2.0 mmol), 2-methylaminopyrimidine-5-carbaldehyde (2.6 mmol), triethylamine (4.0 mmol) and 3 drops of acetic acid in dry dichloromethane (20 mL) was stirred at room temperature for 3 hours. Then sodium triacetoxyborohydride (6.0 mmol) was added in portions and stirring was continued for 48 hours (monitored by TLC). The mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL), and the product was extracted with dichloromethane (2×10 mL). The extracts were washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo to give a crude product. Purification via column chromatography (silica gel, ethyl acetate/hexane) afforded 6-[1-(2-methylaminopyrimidin-5-ylmethyl)-piperidin-4-yl]-2-piperidin-1-yl-pyrimidin-4-ol (Compound IIc, 637 mg, 83%).

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours
  3. customThe mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL)
  4. extractionthe product was extracted with dichloromethane (2×10 mL)
  5. washThe extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customto give a crude product
  9. customPurification via column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d58d3e82003d49929b2016c145809bbf
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349833B2

Reaction notes

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