Potassium Hydroxide → N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409072Notes

Reaction equation

HRID 2409072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:28](S(C3C=CC(C)=CC=3)(=O)=O)[CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH2:24]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:28][CH:27]=[CH:26][C:5]2=[N:6][C:7]=1[CH:8]([NH:10][C:11]1[N:16]=[C:15]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:24][CH2:25]3)[NH:20][N:19]=2)[CH:14]=[CH:13][N:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86689873N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 71611845N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamineYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N2-(1-(6-chloro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (320 mg, 0.58 mmol) in methanol (5 mL) was added an aqueous solution of KOH (2 N, 5 mL). The mixture was heated at 100° C. for 3 h. The reaction mixture was quenched with a saturated NH4Cl solution and extracted with EtOAc. The extract was washed with H2O, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 30 mg (26%) of N2-(1-(6-chloro-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine as white solid. 1H NMR (500 MHz, CD3OD): δ 11.93 (s, 1H), 11.41 (s, 1H), 9.40 (m, 1H), 7.80 (d, 2H), 7.69 (s, 1H), 6.60 (m, 2H), 6.27 (d, 2H), 5.63 (m, 1H), 1.88 (s, 1H), 1.45 (d, 3H), 0.94 (m, 2H), 0.71 (m, 2H); MS (ESI): m/z=395.1 [M+1]+.

Workup

  1. customThe reaction mixture was quenched with a saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe extract was washed with H2O
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-b56d924bed254d4cbe51f2e70ab85e9d
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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