Hydrazine hydrate (1:1) → [4-(5-Amino-2,4-dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine

HRID 855617Notes

Reaction equation

HRID 855617 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([N+:22]([O-])=O)=[C:5]([CH3:21])[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[N:8]=1.O.NN>CCO>[NH2:22][C:4]1[NH:3][C:2]([CH3:1])=[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:8]=2)[C:5]=1[CH3:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 65393144-(2,4-dimethyl-5-nitro-1H-pyrrol-3-yl)-N-(4-fluorophenyl)pyrimidin-2-amine

Product 1

HCID 9879283[4-(5-Amino-2,4-dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amineYield 33.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[4-(2,4-Dimethyl-5-nitro-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine (45 mg, 0.14 mmol) was dissolved in EtOH (3 mL) and 10% Pd(C) catalyst (10 mg) was added, followed by hydrazine hydrate (48 μL of a 55% w/w aq solution, 0.84 mmol). The mixture was heated at reflux for 18 h. The cooled mixture was filtered through a pad of Celite filter aid and the filtrate was evaporated in vacuo. The residue was purified by SiO2 chromatography (20:1 EtOAc/2 M ammonia in MeOH) to afford the title compound (14 mg) as a yellow solid. M.p. 227–231° C. MS: [M+H]+=397.8 (C16H16FN5 requires 297.3). 1H-NMR (CDCl3) δ: 1.98 (s, 3H, CH3), 2.37 (s, 3H, CH3), 4.86 (br. s, 2H, NH2), 6.65 (d, 1H, J=4.9 Hz, pyrimidinyl-H), 7.03 (t, 2H, J=8.3 Hz, Ph-H), 7.49 (br. s, 2H, NH), 7.58–7.61 (m, 2H, Ph-H), 8.53 (d, 1H, J=4.9 Hz, pyrimidinyl-H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. filtrationThe cooled mixture was filtered through a pad of Celite
  4. filtrationfilter aid
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was purified by SiO2 chromatography (20:1 EtOAc/2 M ammonia in MeOH)

Sources & evidence

ORD record
ord-a8c068e2a3604ebca0d656f1cd1225bc
Source dataset
uspto-grants-2007_08
Patent number
US07262202B2

Reaction notes

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