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

HRID 1930396Notes

Reaction equation

HRID 1930396 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([C:10](OCC)=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([NH:3][C:4]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1)[CH3:2]

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 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate (19.5 g, 81.9 mmol) in anhydrous THF (100 mL) was added LiAlH4 (12.3 g, 327.6 mmol) in portions at 0° C. under N2 atmosphere. After stirring for 30 min, the reaction was quenched with water and then 2N aqueous NaOH as added. The suspension was filtered and the filtrate was concentrated to afford (4-(ethylamino)-2-(methylthio)pyrimidin-5-yl)methanol (15 g, 92.0% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.78 (s, 1 H), 6.74 (t, J=4.8 Hz, 1 H), 5.05 (t, J=5.2 Hz, 1 H), 4.26 (d, J=5.2 Hz, 2 H), 3.36 (m, 2 H), 2.37 (s, 3 H), 1.10 (m, 3 H).

Workup

  1. customthe reaction was quenched with water
  2. addition2N aqueous NaOH as added
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab89a756227a4f4cb2e2176390d981b9
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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