(4-(Isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol → HCID 10727218, compound

HRID 1930406Notes

Reaction equation

HRID 1930406 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=1)([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH:1]([NH:4][C:5]1[C:10]([CH:11]=[O:12])=[CH:9][N:8]=[C:7]([S:13][CH3:14])[N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 10536552(4-(Isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol

Product 1

HCID 10727218HCID 10727218, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(isopropylamino)-2-(methylthio)pyrimidin-5-yl)methanol (13.5 g, 63.4 mmol) in DCM (100 mL) was added manganese(IV) oxide (45 g, 0.5 mol), and the mixture was stirred at RT overnight. The reaction mixture was filtered and the filtrate was concentrated to give the 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carbaldehyde (12.2 g, 91% yield), which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6): δ 9.71 (s, 1 H), 8.50 (s, 1 H), 8.41 (d, J=7.2 Hz, 1 H), 4.33 (m, 1 H), 2.47 (s, 3 H), 1.21 (d, J=6.4 Hz, 6 H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f1f24a5d8a4944e9860743a3aa8a557c
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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