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4-Chlorobenzyl alcohol → 6-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one

HRID 2059866
Notes
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Reaction equation

HRID 2059866 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1.Cl[C:13]1[N:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])=[C:21]([O:31][CH3:32])[CH:20]=2)[C:15](=[O:33])[CH:14]=1>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:13]2[N:18]=[CH:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])=[C:21]([O:31][CH3:32])[CH:20]=3)[C:15](=[O:33])[CH:14]=2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 585799166-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-pyrimidin-4(3H)-one

Product 1

HCID 469267226-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-oneYield 5.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Sodium hydride (13 mg, 0.32 mmol) was added to a solution of (4-chlorophenyl)methanol (46 mg, 0.32 mmol) in THF (1 mL) under nitrogen. The mixture was stirred at RT for 1 hour, then 6-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one Part A (35 mg, 0.108 mmol) was added and stirred for 45 min at RT. The reaction was quenched with MeOH (0.5 mL), diluted with EtOAc, washed with saturated NH4Cl, dried (Na2SO4), and concentrated. The residue was subjected to ISCO flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient). The product was then re-purified using HPLC (C18 column/10:90 to 90:10 MeOH—H2O) to afford the title compound 6-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one H-1 (2.5 mg, 5.2% yield). LC/MS 431 (M+H)+, tR 0.91 min (method 5); 1H NMR (400 MHz, chloroform-d) δ 6.04 (1H, s), 7.38 (4H, s), 7.00 (1H, d), 6.79-6.89 (2H, m), 5.85 (1H, s), 5.27 (2H, s), 3.87 (3H, s), 3.86 (2H, s), 1.36 (6H, s).

Workup

  1. stirringstirred for 45 min at RT
  2. customThe reaction was quenched with MeOH (0.5 mL)
  3. additiondiluted with EtOAc
  4. washwashed with saturated NH4Cl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was then re-purified

Sources & evidence

ORD record
ord-8486411d6fbb44d0bb669369d087cd7a
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08278316B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes