Ammonium Hydroxide → HCID 58296335, compound

HRID 390040Notes

Reaction equation

HRID 390040 reaction equation
[CH3:1][C:2]1[C:7]([C:8](O)=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:5]=[C:4]([S:19][CH3:20])[N:3]=1.C([N:24](C(C)C)CC)(C)C.[OH-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[C:7]([C:8]([NH2:24])=[O:9])=[C:6]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:5]=[C:4]([S:19][CH3:20])[N:3]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 58296327HCID 58296327, compound

Product 1

HCID 58296335HCID 58296335, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarboxylic acid (1.71 g, 5.90 mmole) in DMF (40 mL) were added o-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyl uroniumhexafluoro phosphate (4.88 g, 12.8 mmol) and diisopropylethylamine (3.83 g, 29.6 mmol). The reaction mixture was stirred for 10 min before ammonium hydroxide (7.2 ml of 28%) was added. The mixture was stirred for additional 20 min and DMF was removed under vacuum. The residue was partitioned between ethyl acetate and water. The insoluble product was collected by filtration and dried under vacuum (0.54 g). The organic phase was separated, washed with 1N NaOH, water and dried over MgSO4. The solvent was removed under vacuum to give additional product (1.03 g) which was combined with the previously obtained precipitated product (1.27 g in total, 74% yield).

Workup

  1. additionwas added
  2. customDMF was removed under vacuum
  3. customThe residue was partitioned between ethyl acetate and water
  4. filtrationThe insoluble product was collected by filtration
  5. customdried under vacuum (0.54 g)
  6. customThe organic phase was separated
  7. washwashed with 1N NaOH, water
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4e5f8b17431a41f9816a89ec6ad3f7c9
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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