HCID 60137814, compound → 1-(5-Fluoro-2-pyrimidinyl)-4-piperidinecarbaldehyde

HRID 423623Notes

Reaction equation

HRID 423623 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 60137814HCID 60137814, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 866387471-(5-Fluoro-2-pyrimidinyl)-4-piperidinecarbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-Fluoro-2-pyrimidinyl)-4-piperidinecarbaldehyde (0.96 g, 60%) was prepared as a white solid from [1-(5-fluoro-2-pyrimidinyl)-4-piperidinyl]methanol (prepared as in Example 152, Step 1, 1.62 g, 7.67 mmol) and PCC (pyridinium chlorochromate, 2.53 g, 11.50 mmol) in CH2Cl2 (36 mL) in a manner similar to Example 146, Step 1. The crude product was purified by chromatography on an ISCO silica gel column using 0 to 20% EtOAc/hexanes to give 1-(5-fluoro-2-pyrimidinyl)-4-piperidinecarbaldehyde as a white solid. 1H NMR (400 MHz, CDCl3): δ 9.68 (s, 1H), 8.20 (s, 2H), 4.55-4.45 (m, 2H), 3.25-3.10 (m, 2H), 2.60-2.45 (m, 1H), 2.05-1.90 (m, 2H), 1.70-1.55 (m, 2H); LRMS (ESI), m/z 210 (M+H).

Workup

  1. customThe crude product was purified by chromatography on an ISCO silica gel column

Sources & evidence

ORD record
ord-30dbeafd8e2c4872ad7dccdcb2a5b26b
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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