Hydrochloric Acid → 2-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMine

HRID 1926591Notes

Reaction equation

HRID 1926591 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[C:7]([CH3:10])=[N:8][CH:9]=1)([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[C:7]([CH3:10])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 46910559N-(2-methyl-5-nitropyridin-3-yl)-4-(pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 469098562-Methyl-N3-(4-(pyridin-3-yl)pyriMidin-2-yl)pyridine-3,5-diaMineYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a flask was added N-(5-nitro-2-methyl-pyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (18.0 g) and THF (200 mL) and the solution was cooled to 0-5° C. To the solution was added LiAlH4 (about 2.2 g in total) in several portions and the mixture was stirred for 2 hours at the same temperature. The reaction mixture was acidified to pH=5-6 using 1N HCl and then extracted with CH2Cl2 (2×100 mL ). The organic extracts were combined, dried, filtrated and concentrated to afford N-(5-amino-2-methylpyrid-3-yl)-4-(pyrid-3-yl)-2-pyrimidinamine (12 g).

Workup

  1. extractionextracted with CH2Cl2 (2×100 mL )
  2. customdried
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ddcdb086ecd74abc80827fa789815c0c
Source dataset
uspto-grants-2012_05
Patent number
US08183242B2

Reaction notes

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