Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate → (4-(Ethylamino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 3220Notes

Reaction equation

HRID 3220 reaction equation
C([O:3][C:4]([C:6]1[C:7]([NH:14][CH2:15][CH3:16])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:15]([NH:14][C:7]1[C:6]([CH2:4][OH:3])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1)[CH3:16]

Participants

4

Reactant 2

HCID 10514260Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10584149(4-(Ethylamino)-2-(methylthio)pyrimidin-5-yl)methanolYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-ethylamino-2-methylthio-5-pyrimidinecarboxylate ethyl ester (8.93 g, 37.1 mmol) in 100 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (2.30 g, 60.5 mmol) in 100 mL of tetrahydrofuran. After 10 minutes, the reaction was carefully quenched with 4.5 mL of water, 4.5 mL of 15% NaOH, and 16 mL of water, and the mixture was stirred for 1.5 hours. The white precipitate was removed by filtration washing with ethyl acetate. The filtrate was concentrated in vacuo and 1:1 hexane:ethyl acetate was added. The solids were collected to give 6.77 g (92%) of 4-ethylamino-2-methylthio-5-pyrimidinemethanol; mp 152°-156° C.

Workup

  1. customthe reaction was carefully quenched with 4.5 mL of water, 4.5 mL of 15% NaOH, and 16 mL of water
  2. customThe white precipitate was removed by filtration
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo and 1:1 hexane
  5. additionethyl acetate was added
  6. customThe solids were collected

Sources & evidence

ORD record
ord-f2375584c8354f2a9aff7eb95f5d470f
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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