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Sodium Hydroxide → (4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 1352742
Notes
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Reaction equation

HRID 1352742 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=2)[C:12]([C:26](OCC)=[O:27])=[CH:11][N:10]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([Cl:25])[CH:18]=2)[C:12]([CH2:26][OH:27])=[CH:11][N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 22025927Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

Product 1

HCID 22025932(4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidin-5-yl)methanol

Reagents, catalysts & solvents

2
HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride 4.15 g in tetrahydrofuran 150 ml is added a solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 67-(1)) 38.32 g in tetrahydrofuran 100 ml at 5–10° C. under ice cooling over a period of 1 hour. After addition the mixture is stirred for a hour without an ice bath. Water 4.15 ml is added under ice cooling thereto, followed by addition of 3N aqueous sodium hydroxide solution 4.15 ml. To the mixture is added water 4.15 ml three times and the mixture is stirred at room temperature for 1 hour. After treating with magnesium sulfate and filtration, the resulting cake-like substances are washed with terahydrofuran. The filtrate is concentrated in vacuo and triturated with ethyl acetate-isopropyl ether. The resulting crystals are filtered and washed well with isopropyl-ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-hydroxymethylpyrimidine as a pale yellow crystalline powder.

Workup

  1. additionAfter addition the mixture
  2. stirringthe mixture is stirred at room temperature for 1 hour
  3. washthe resulting cake-like substances are washed with terahydrofuran
  4. concentrationThe filtrate is concentrated in vacuo
  5. customtriturated with ethyl acetate-isopropyl ether
  6. filtrationThe resulting crystals are filtered
  7. washwashed well with isopropyl-ether

Sources & evidence

ORD record
ord-8a46d2f9b0334e9fb38bb7b218e06258
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220736B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes