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

HRID 599332Notes

Reaction equation

HRID 599332 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 98.3%

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 LiAlH4 (6.1 g, 0.16 mol) in portions at 0° C. under N2 atmosphere. The reaction mixture was stirred an additional 30 min at RT and was quenched by the addition of water (6 mL) followed by aqueous 2 N 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% yield), which was used without further purification. 1H NMR (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. customwas quenched by the addition of water (6 mL)
  2. filtrationThe suspension was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-79890d7f59f241c09df6365a92818a22
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…