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Triethylamine → 6-[1-[(2-aminopyrimidin-5-yl)methyl]piperidin-4-yl]-2-piperidin-1-yl-1H-pyrimidin-4-one

HRID 1526485
Notes
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Reaction equation

HRID 1526485 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:12]=[C:11]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[N:10]=[C:9]([OH:19])[CH:8]=2)[CH2:3][CH2:2]1.[NH2:20][C:21]1[N:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][N:22]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[NH2:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:1]2[CH2:6][CH2:5][CH:4]([C:7]3[N:12]=[C:11]([N:13]4[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]4)[N:10]=[C:9]([OH:19])[CH:8]=3)[CH2:3][CH2:2]2)=[CH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 7690972-Aminopyrimidine-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 1785156812-piperidin-1-yl-6-piperidin-4-yl-1H-pyrimidin-4-one

Product 1

HCID 1785084076-[1-[(2-aminopyrimidin-5-yl)methyl]piperidin-4-yl]-2-piperidin-1-yl-1H-pyrimidin-4-oneYield 82%

Reagents, catalysts & solvents

2
HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-piperidin-4-yl-2-piperidin-1-yl-pyrimidin-4-ol (2.0 mmol), 2-amino-pyrimidine-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-Amino-pyrimidin-5-ylmethyl)-piperidin-4-yl]-2-piperidin-1-yl-pyrimidin-4-ol (606 mg, 82%)

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-83ffd88e6b51487ba63edbb0e4311f93
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09085585B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes