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

HRID 1696439Notes

Reaction equation

HRID 1696439 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-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[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 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (30 g, 132 mmol) in THF (300 mL) was added LiAlH4 powder (7.5 g, 198 mmol) at RT. After 1 h, the reaction was carefully quenched with H2O (10 mL) and 10% NaOH (7 mL). The mixture was stirred for 1 h and then filtered. The filtrate was concentrated to give crude (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (22.0 g, 90% yield), which was used in the next reaction without further purification. 1H NMR (300 MHz, DMSO-d6): δ 7.79 (s, 1H), 6.79 (m, 1H), 5.04 (t, J=5.4 Hz, 1H), 4.27 (d, J=5.4 Hz, 2H), 2.83 (d, J=4.8 Hz, 3H), 2.40 (s, 3H).

Workup

  1. customthe reaction was carefully quenched with H2O (10 mL) and 10% NaOH (7 mL)
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ebe0c33560c14dedaadfa3dc66115337
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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