Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[C:9]1([CH2:15][O-:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na+]>>[CH2:15]([O:16][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
Procedure
6-Chloropyrimidin-4-amine (500 mg, 3.86 mmol) and sodium phenylmethanolate (1 M solution in benzyl alcohol, 4.67 mL, 4.67 mmol) were heated at 120° C. for 16 hrs. 6-(Benzyloxy)pyrimidin-4-amine (210 mg, 27% yield) was isolated as clear oil following HPLC purification (Phenomenex Axia Luna 5 micron 30×100 mm) 30% B (Solvent B=90% MeOH-10% H2O-0.1% TFA) to 100% B in A (Solvent A=10% MeOH-90% H2O-0.1% TFA). The purified material (a TFA salt) was converted to its free base by dissolving in ethyl acetate (20 mL) and washing with saturated NaHCO3 (20 mL) for use in the next step. LC/MS (Phenomenex Luna 5 micron C18 4.6×30 mm, 0 to 100 B in 2 min with 1 min hold time, Flow rate=5 mL/min, detection at 254 nm, Solvent A: 10% methanol/90% water/0.1% TFA; Solvent B: 10% water/90% methanol/0.1% TFA). Rt=0.96 (M+H=202.24).
Sources & evidence
- ORD record
- ord-d7104f18a0364c30a7071d4f90bfc1f0
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389527B2
Linked notes
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