Hydroxyamine hydrochloride → HCID 67538239, compound

HRID 1192398Notes

Reaction equation

HRID 1192398 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH:20]3[CH2:22][CH2:21]3)=[C:18]([N:23]=C(C3C=CC=CC=3)C3C=CC=CC=3)[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.NO.CC([O-])=O.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([CH:20]3[CH2:22][CH2:21]3)=[C:18]([NH2:23])[N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 86598735HCID 86598735, compound

Product 1

HCID 67538239HCID 67538239, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-[6-(Benzhydrylidene-amino)-5-cyclopropyl-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (1.60 g, 3.31 mmol) in MeOH (70 mL) was added hydroxylamine hydrochloride (0.41 g, 6.0 mmol) and NaOAc (0.65 g, 7.9 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between 0.1N NaOH and DCM. The organic layer was dried and concentrated. The residue was purified by column (DCM:MeOH, 20:1) to give 4-(6-Amino-5-cyclopropyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.00 g, 95%) as a colorless syrup. 1H NMR (CDCl3, 400 MHz) δ 8.12 (s, 1H), 4.97 (s, 2H), 3.52 (m, 4H), 3.50 (m, 4H), 1.48 (s, 9H), 1.44 (m, 1H), 1.02 (m, 2H), 0.64 (m, 2H). LCMS (APCI+) m/z 320 [M+H]+; Rt=2.51 min.

Workup

  1. customthe reaction mixture was partitioned between 0.1N NaOH and DCM
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by column (DCM:MeOH, 20:1)

Sources & evidence

ORD record
ord-e03d2b0f85f94301af04750661dd8649
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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