Hydrazine hydrate (1:1) → HCID 178503430, compound

HRID 1809680Notes

Reaction equation

HRID 1809680 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=O)=[CH:4][N:3]=1.O.[NH2:20][NH2:21].CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[NH:20][N:21]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 86667955(2,4-Dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone

Product 1

HCID 178503430HCID 178503430, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (2,4-dichloro-pyrimidin-5-yl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone (9.52 g, 31.6 mmol) in THF (100 mL) was added hydrazine hydrate (2.3 g, 46 mmol) and DIPEA (5.9 g, 45.7 mmol). The mixture was heated at 50° C. for 4 hours, then concentrated to dryness. The resulting precipitate was collected by filtration and washed with water to give 6-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine as a yellow solid. (Yield 7.8 g, 88%).

Workup

  1. concentrationconcentrated to dryness
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-f647dc0412a44394baa2c816168c0f4e
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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