Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate → (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 3169

Reaction equation

HRID 3169 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:14][CH3:15])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:15][NH:14][C:7]1[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1

Participants

4

Reactant 2

HCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10679092(4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (4.36 g, 19.3 mmol) in 60 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (1.10 g, 29.0 mmol) in 40 mL of tetrahydrofuran. After 10 minutes the reaction was carefully quenched with 2 mL of water, 2 mL of 15% NaOH, and an additional 7 mL of water. The mixture was stirred for 1 hour, and the white precipitate which had formed was removed by filtration, and was washed with ethyl acetate. The filtrate was concentrated in vacuo and 3:1 hexane:ethyl acetate was added. The solids were collected to give 2.99 g (84%) of 4-methylamino-2-methylsulfanyl-5-pyrimidinemethanol; mp 155°-157° C.

Workup

  1. customAfter 10 minutes the reaction was carefully quenched with 2 mL of water, 2 mL of 15% NaOH
  2. customthe white precipitate which had formed
  3. customwas removed by filtration
  4. washwas washed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo and 3:1 hexane
  6. additionethyl acetate was added
  7. customThe solids were collected

Sources & evidence

ORD record
ord-abfc9b5568f94a61bc5a0e552cd345d3
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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