Yield:-

Reaction Conditions:

Stage #1:3-methyl-4-nitro-1H-pyrazole;methyl iodide with hydrogen;sodium hydride in tetrahydrofuran;mineral oil at 0 - 27; for 4 h;
Stage #2: with hydrogen;palladium(II) hydroxide in ethanol for 14 h;Overall yield = 67 %; Overall yield = 3 g;

Steps:

Synthesis of a mixture of 1,3-dimethyl-1H-pyrazol-4-amine and 1,5-dimethyl-1H- pyrazol-4-amine (Precursor-25)
To a stirred solution 49-a and 49-b (5.7 g, 4.04 mmol) in ethanol (50 mL), 0.8 g of Pd(OH)2 was added and then stirred reaction under H2 gas atm for 14h. After the completion of reaction (TLC monitoring), the solution was filtered through celite bed, washed with methanol.and concentrated the solvent to get a crude mixture precursor-25 (3.0 g, 67% yield) that was carried as such for the next step without further purification. ‘HNMR (400 MHz, DMSO-d6): ? 6.81 (s, 11-1), 3.57 (s, 3H), 3.52 (s, 2H), 2.05 (s, 3H). MS: 112.08 (M+H).

References:

JUBILANT BIOSYS LIMITED;VENKATESHAPPA, Chandregowda;SIVANANDHAN, Dhanalakshmi;BAKTHAVATCHALAM, Rajagopal;KETHIRI, Raghava Reddy;VISWANADHAN, Vellarkad Narayana;GIRI, Sanjeev WO2015/25197, 2015, A1 Location in patent:Paragraph 000120