HCID 10491237, compound → (4-(Isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 1930405Notes

Reaction equation

HRID 1930405 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11](OCC)=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1]([NH:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10491237HCID 10491237, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10536552(4-(Isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanolYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (16.4 g, 64.4 mmol) in anhydrous THF (100 mL) was added LAH (6.1 g, 0.16 mol) in portions at 0° C. under N2 atmosphere, then the reaction mixture was stirred at r.t. for 30 min. The reaction was quenched by the addition of water (6 mL) followed by aqueous solution of 2N NaOH (6 mL). The suspension was filtered and the filtrate was concentrated to give (4-(isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol (13.5 g, 98.4% yield), which was used in next step without further purification. 1HNMR (400 MHz, DMSO-d6): δ 7.79 (s, 1 H), 6.37 (d, J=7.6 Hz, 1 H), 5.10 (t, J=5.6 Hz, 1 H), 4.28-4.20 (m, 3 H), 2.38 (s, 3 H), 1.13 (d, J=6.4 Hz, 6 H).

Workup

  1. customThe reaction was quenched by the addition of water (6 mL)
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d25903d80d4744eabcea82687f40558a
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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