Tetrahydrofuran → 6-(2-Amino-4-pyrimidinyl)-4-(methyloxy)-1H-indazol-3-amine

HRID 2367203Notes

Reaction equation

HRID 2367203 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[C:14](OC)[C:11]([C:12]#[N:13])=[C:10](F)[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[OH2:19].[NH2:20][NH2:21].[CH2:22]1COCC1>>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:15]=[C:14]3[C:11]([C:12]([NH2:13])=[N:20][NH:21]3)=[C:10]([O:19][CH3:22])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 585044614-(2-Amino-4-pyrimidinyl)-2-fluoro-6-(methyloxy)benzonitrile

Product 1

HCID 462143136-(2-Amino-4-pyrimidinyl)-4-(methyloxy)-1H-indazol-3-amineYield 49%

Conditions

Temperature
90 °C

Procedure

To a slurry of 4-(2-amino-4-pyrimidinyl)-2-fluoro-6-(methyloxy)benzonitrile (0.20 g, 0.82 mmol) in THF (2 mL) was added hydrazine monohydrate (1.3 mL), and the resulting mixture was stirred at 90° C. until the starting material was consumed as judged by LCMS (˜12 hours). The reaction mixture was concentrated to afford the title compound (102 mg, 49%) as a bright yellow solid. LC-MS (ES) m/z=257 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.94 (s, 3H), 5.06 (s, 2H), 6.65 (s, 2H), 6.97 (s, 1H), 7.16 (d, J=5.3 Hz, 1H), 7.54 (d, J=1.0 Hz, 1H), 8.30 (d, J=5.3 Hz, 1H), 11.67 (bs, 1H).

Workup

  1. customwas consumed
  2. customas judged by LCMS (˜12 hours)
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-2142675385534c5595f02d8b6926d28d
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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