Sodium Hydroxide → N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409074Notes

Reaction equation

HRID 2409074 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16]CC4C5C=NN(S(C6C=CC(C)=CC=6)(=O)=O)C=5C=CN=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86689874N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine

Product 1

HCID 86689872N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-tosyl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine (400 mg, 0.80 mmol) in MeOH (5 mL) was added aqueous NaOH (2 N, 5 mL). The mixture was heated at reflux overnight. The reaction mixture was extracted with EtOAc (100 mL×3), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by preparative HPLC to afford 30 mg (6.3%) of N241H-pyrazolo[4,3-c]pyridin-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as yellow solid. 1H NMR (500 MHz, DMSO-d4) δ 9.44 (brs, 1H), 8.32 (brs, 1H), 8.23 (d, J=6 Hz, 1H), 7.80 (d, J=5 Hz, 1H), 7.40 (d, J=6 Hz, 1H), 6.14-5.99 (m, 2H), 4.87 (d, J=5.5 Hz, 2H), 1.80 (s, 1H), 0.88-0.87 (m, 2H), 0.66 (s, 2H); MS (ESI): m/z=348.1 [M+1]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. extractionThe reaction mixture was extracted with EtOAc (100 mL×3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-02d5d73bcf0a477bb8a73e372f9eb9cb
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

Loading…