[NH4+].Cl[C:3]1[N:8]=[C:7]([OH:9])[C:6]([F:10])=[C:5]([CH2:11][CH3:12])[N:4]=1.C(O)C>[Pd].O>[CH2:11]([C:5]1[N:4]=[CH:3][N:8]=[C:7]([OH:9])[C:6]=1[F:10])[CH3:12]To a mixture of the compound of part (iii) (34 kg), ethanol (170 L) and water (5 kg) was added 5% w/w palladium-on-carbon (50% w/w water content) (3.4 kg) and the mixture hydrogenated at 50° C. and 345 kPa (50 psi) until completion of the reaction. Water (10.5 L) was added and the catalyst removed by filtration. The filtrate was concentrated under reduced pressure to a small volume and extracted with dichloromethane (2×58 L). The combined organic extracts were concentrated under reduced pressure and toluene (150 L) added. The mixture was concentrated under reduced pressure to 50 L in volume, toluene (50 L) added and cooled to 4° C. for 4 hours. The precipitated product was collected by filtration, washed with toluene (10 L) and dried (Yield=20 kg), m.p. 112-4° C.
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