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5-Ethynylpyrimidine → HCID 69123269, compound

HRID 349262
Notes
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Reaction equation

HRID 349262 reaction equation
C([Mg]Br)C.[C:5]([C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1)#[CH:6].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:24][N:23]=[C:22]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C:21]=1[CH:33]=[O:34]>C(OCC)C.C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:24][N:23]=[C:22]([CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C:21]=1[CH:33]([OH:34])[C:6]#[C:5][C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14751945-EthynylpyrimidineHCID 86601216HCID 86601216, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 69123269HCID 69123269, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Add 3M ethylmagnesium bromide (36 mL, 109 mmol) in diethyl ether to a 0° C. solution of 5-ethynyl-pyrimidine (8.1 g, 77 mmol) in THF (75 mL). Add 5-(2-chloro-phenyl)-3-(tetrahydro-pyran-2-yloxymethyl)-isoxazole-4-carbaldehyde (10 g, 31 mmol) in THF (75 mL) and stir 15 h at RT. Quench the reaction with 1N HCl and extract with diethyl ether (2×150 mL). Wash the organic phase with brine (150 mL), dry over sodium sulfate, filter and concentrate under reduced pressure. Purification by flash chromatography (silica gel, 1:1 to 3:7 hexanes/EtOAc) gives the title compound (5.3 g, 40%): 1H NMR (300 MHz, CDCl3) δ 9.18 (s, 1H), 8.35 (s, 2H), 7.44–7.62 (m, 4H), 5.65 (t, J=14 Hz, 1H), 5.08–5.28 (m, 1H), 4.80–4.95 (m, 2H), 4.42–4.60 (m, 1H), 3.80–4.01 (m, 1H), 3.51–3.68 (m, 1H), 1.54–1.90 (m, 6H); TLC Rf=0.20 (3:7 Hexanes:EtOAc).

Workup

  1. customQuench
  2. customthe reaction with 1N HCl
  3. extractionextract with diethyl ether (2×150 mL)
  4. washWash the organic phase with brine (150 mL)
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurification by flash chromatography (silica gel, 1:1 to 3:7 hexanes/EtOAc)

Sources & evidence

ORD record
ord-d495079a1a36413d94f0a1d1ccd5d0db
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179804B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes