Reaction equation
I[C:2]1[CH:10]2[CH:5]([N:6]=[CH:7][N:8]=[C:9]2[NH:11][CH3:12])[N:4]([CH:13]([CH3:15])[CH3:14])[CH:3]=1.COC(O)C(O)OC.O[C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH:13]([N:4]1[CH:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:11][CH3:12])[CH:10]2[C:2]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]1)([CH3:15])[CH3:14]Participants
Procedure
7,7a-Dihydro-5-iodo-7-isopropyl-N-methyl-4aH-pyrrolo[2,3-d]pyrimidin-4-amine (0.15 g, 0.475 mmol) from above was placed in a 50 ml round bottom flask, whereupon 12 ml dimethoxy ethyleneglycol was added. 3-Hydroxyphenylboronic acid (0.262 g, 1.9 mmol pre-dissolved in 3.3 ml ethanol) was added at once, and was followed by 1.9 ml saturated aqueous sodium carbonate. Pd0(PPh3)4 (55 mg, 47 umol) was added to the reaction, the vessel was purged with argon, and set to stir at 80 C for 48 h. The reaction was subsequently cooled, and filtered through a bed of celite. The filtrate was evaporated in vacuo, and the residual material was adhered to silica gel using ethyl acetate as solvent. Silica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions yielded the desired product (94.8 mg, 70.7% yield). 1H NMR (399.6 MHz, d6-DMSO) δ 1.76 (6H, d, J=6.8 Hz), 5.03 (3H, d, J=4.8 Hz), 5.34 (1H, sp, J=6.4 Hz), 5.53 (1H, q, J=4.8 Hz), 6.73 (1H, m), 6.85 (1H, m), 7.25 (1H, app t, J=7.6 Hz), 7.37 (1H, s), 7.59 (1H, s).
Workup
- additionwas added
- customthe vessel was purged with argon
- temperatureThe reaction was subsequently cooled
- filtrationfiltered through a bed of celite
- customThe filtrate was evaporated in vacuo
- customSilica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions
Sources & evidence
- ORD record
- ord-e5d4db14a61d4238a92e3ac9cb49c7b1
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429596B2
Linked notes
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