Sodium Hydroxide → HCID 67063020, compound

HRID 599259Notes

Reaction equation

HRID 599259 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]=[CH:15][C:16]2[C:17]([NH:24][CH3:25])=[N:18][C:19]([S:22][CH3:23])=[N:20][CH:21]=2)=[CH:10][C:9]=1[N+:26]([O-:28])=[O:27].[OH-].[Na+]>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH2:15][C:16]2[C:17]([NH:24][CH3:25])=[N:18][C:19]([S:22][CH3:23])=[N:20][CH:21]=2)=[CH:10][C:9]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67063015HCID 67063015, compound

Product 1

HCID 67063020HCID 67063020, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of LiAlH4 (1.3 g, 34 mmol) in anhydrous THF at 0° C. was added the above 5-((4-fluoro-3-nitrophenylimino)methyl)-N-methyl-2-(methylthio)pyrimidin-4-amine portionwise over 20 min. After the addition was complete, the mixture was stirred at 0° C. for 30 min. Aqueous 10% NaOH (2 mL) was added and the resultant precipitate was removed by filtration. The filtrate was concentrated under reduced pressure to give 5-((4-fluoro-3-nitrophenylamino)methyl)-N-methyl-2-(methylthio)pyrimidin-4-amine (6.0 g, 56% yield) as a brown solid. 1H NMR (300 MHz, DMSO-d6): δ 7.84 (s, 1 H), 7.28 (dd, J=6.6, 8.4 Hz, 1 H), 7.17 (m, 1 H), 7.03 (m, 1 H), 6.42 (t, J=3.9 Hz, 1 H), 4.00 (d, J=3.9 Hz, 2 H), 2.82 (d, J=4.8 Hz, 3 H), 2.39 (s, 3 H); MS (ESI) m/z: 324.1 (M+H+).

Workup

  1. additionAfter the addition
  2. customthe resultant precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a30fec388694fd6be522711476b9fab
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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