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

HRID 599329Notes

Reaction equation

HRID 599329 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-e7f0c6f510bd45fa8187b3b85ab5c303
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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