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Water → 5-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one

HRID 2108856
Notes
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Reaction equation

HRID 2108856 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[N:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[C:26](=[O:33])[CH:27]=[C:28]([CH2:31][OH:32])[O:29][CH:30]=1.O>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[C:26](=[O:33])[CH:27]=[C:28]([CH2:31][OH:32])[O:29][CH:30]=2)=[N:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 179758375-(5-Bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 178517962HCID 178517962, compound

Product 1

HCID 179757985-(5-(quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneYield 26%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

Quinazolin-4-ol (1.0 g, 6.84 mmol) was dissolved in DMF (7 mL). Cs2CO3 (2.23 g, 6.84 mmol) was added at RT and the mixture was stirred for 10 min. A solution of 5-(5-bromo-pentyloxy)-2-hydroxymethyl-pyran-4-one 10 (1.90 g, 6.52 mmol) in DMF (7 mL) was added via syringe. This mixture was stirred at 50° C. for 2 h. Water (150 mL) was added and the mixture extracted with EtOAc (2×100 mL), washed with water (3×100 mL), brine (3×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=95:5. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 15 was obtained (0.61 g, 26% yield) as a pale yellow solid.

Workup

  1. stirringThis mixture was stirred at 50° C. for 2 h
  2. extractionthe mixture extracted with EtOAc (2×100 mL)
  3. washwashed with water (3×100 mL), brine (3×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

Sources & evidence

ORD record
ord-ec877a2919ae4c9ca88a301d964f4269
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07514432B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes