Sodium Iodide → HCID 135995179, compound

HRID 1622040Notes

Reaction equation

HRID 1622040 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4](=[O:24])[CH2:5][C:6]1[C:7]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)[CH3:2].[Na+].[I-:28]>CO>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4](=[O:24])[CH2:5][C:6]1[C:7]([C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[C:21]([I:28])[CH:22]=2)=[N:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[N:11][C:10]=12)[CH3:26]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 135948779Pyrazolo[1,5-a]pyrimidine-3-acetamide,N,N-diethyl-2-(4-hydroxyphenyl)-5,7-dimethyl-

Product 1

HCID 135995179HCID 135995179, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3 (100 mg, 0.28 mmol) in MeOH (15 mL) was added NaI (52 mg, 0.35 mmol) and chloroamine-T hydrate (80 mg, 0.35 mmol). The reaction mixture was stirred for 1 h and then concentrated under vacuum. The residue was purified by column chromatography (CH2Cl2/MeOH, 20:1 (v/v), as eluent) to yield 4 (60 mg, 45% yield). 1H NMR (CD3OD, 400 MHz) δ 1.16 (t, J=7.2 Hz, 3H), 1.29 (t, J=7.2 Hz, 3H), 2.57 (s, 3H), 2.76 (s, 3H), 3.44 (q, J=7.2 Hz, 2H), 3.59 (q, J=7.2 Hz, 2H), 3.97 (s, 2H), 6.80 (s, 1H), 6.92 (d, J=8 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 8.01 (s, 1H). ESI MS m/z: [M+H]+. C20H24IN4O2: calculated 479.1. found 479.1.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by column chromatography (CH2Cl2/MeOH, 20:1 (v/v), as eluent)

Sources & evidence

ORD record
ord-17612c13bbfe470b98bc3683caacc9a3
Source dataset
uspto-grants-2014_07
Patent number
US08778304B2

Reaction notes

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