Hydrochloric Acid → HCID 178517769, compound

HRID 1500047Notes

Reaction equation

[CH2:1]([N:8](C)[C:9]1[C:14]([F:15])=[CH:13][N:12]=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:18].[K+].Cl.O1CCOC[CH2:22]1.O>O>[CH2:2]([CH2:1][NH:8][C:9]1[C:14]([F:15])=[CH:13][N:12]=[C:11]([OH:18])[N:10]=1)[C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of N-benzyl-2-chloro-5-fluoro-N-methylpyrimidin-4-amine (0.075 g, 0.30 mmol) in dioxane/H2O (1:1, 2 mL total volume) was added KOH (0.17 g, 3.0 mmol) and the mixture was warmed to 100° C. and stirred for 72 h. The reaction was diluted with H2O (5 mL) and the pH was adjusted to 7 with 2 N HCl. The resulting white precipitate was collected by vacuum filtration, but the majority of the product remained in the aqueous phase. The solid and filtrate were combined and the solvent was removed by azeotropic distillation with CH3CN on the rotary evaporator. The residue was dissolved/suspended in CH2Cl2 (25 mL), adsorbed onto Celite (3.0 g) and purified by flash chromatography (24 g SiO2, MeOH/CH2Cl2 gradient) to give 4-(benzylmethylamino)-5-fluoropyrimidin-2-ol (0.016 g, 23%) as a white solid: mp 175-178° C.; 1H NMR (300 MHz, CDCl3) δ 12.72 (s, 1H), 7.42-7.14 (m, 6H), 4.88 (s, 2H), 3.20 (d, J=3.2, 3H); MS (ESI) m/z 235 (M+2)+, m/z 232 (M−H)−.

Workup

filtrationThe resulting white precipitate was collected by vacuum filtration
customthe solvent was removed by azeotropic distillation with CH3CN on the rotary evaporator
custompurified by flash chromatography (24 g SiO2, MeOH/CH2Cl2 gradient)

Sources & evidence

ORD record: ord-3001c60da66947c8a0ade7d55eac6f1b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09204653B2

Reaction notes

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