Sodium Carbonate → HCID 178482401、化合物

HRID 33412

反応式

HRID 33412 の反応式
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]

参加物

5

反応物 4

HCID 10340Sodium CarbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 21263609Dimethoxy ethylene glycolHCID 178482404HCID 178482404、化合物

生成物 1

HCID 178482401HCID 178482401、化合物収率 74.4%

実験手順

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).

後処理

  1. additionwas added
  2. customthe vessel was purged with argon
  3. temperatureThe reaction was subsequently cooled
  4. filtrationfiltered through a bed of celite
  5. customThe filtrate was evaporated in vacuo
  6. customSilica gel chromatography (ethyl acetate:hexanes) and evaporation in vacuo of the requisite fractions

出典と根拠

ORDレコード
ord-e5d4db14a61d4238a92e3ac9cb49c7b1
出典データセット
uspto-grants-2008_09
特許番号
US07429596B2

関連ノート

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