Yield:-

Reaction Conditions:

Stage #1:1-methyl-1H-pyrazole-3-carboxamide with borane-THF in tetrahydrofuran at 65; for 18 h;
Stage #2: with hydrogenchloride;methanol;water in tetrahydrofuran

Steps:

30
Description 30; (1-Methvl-pvrazole-3-methanamine) A solution of Description 29 (0.08g) in anhydrous tetrahydrofuran (5ml) was treated with a 1 M solution of borane/tetrahydrofuran complex in tetrahydrofuran (3. 5mi) and the mixture was heated at 65°C for 18hrs. On cooling the mixture was cautiously quenched by dropwise addition of methanol followed by 2N hydrochloric acid. The solvents were removed by evaporation, and the residue was made basic with triethylamine and concentrated in vacuo. The mixture was dissolved in a small volume of methanol applied onto a sulphonic acid SCX ion exchange cartridge (10g), eluting with methanol followed by 10% 0. 880 ammonia in methanol. The basic fraction was evaporated in vacuo to give the title compound (0.054g) as a colourless oil which also contained-10% of 1 H- pyrazole-3-methanamine [CAS No. 37599-58-9]. 1H nmr (D4MeOH), No. 3. 84 (2H, s, CH2) ; 3. 86 (3H, s, Me); 6.28 (1H , m, Ar); 7.53 (1H, m, Ar).

References:

GLAXO GROUP LIMITED WO2003/82861, 2003, A2 Location in patent:Page/Page column 50-51