p-Toluenesulfonic acid monohydrate → (2-Benzyl-6-p-tolyl-pyrimidin-4-yl)-methanol

HRID 1917267ノート

反応式

HRID 1917267 の反応式
[CH2:1]([C:8]1[N:13]=[C:12]([CH2:14][O:15]C2CCCCO2)[CH:11]=[C:10]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO>[CH2:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 666164432-Benzyl-4-(tetrahydro-pyran-2-yloxymethyl)-6-p-tolyl-pyrimidine

生成物 1

HCID 66616359(2-Benzyl-6-p-tolyl-pyrimidin-4-yl)-methanol収率 99%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of the product from Step A (2.0 g, 5.3 g) in MeOH (30 mL) was added p-TsOH.H2O. After 18 h, the reaction was diluted with satd. aq. NaHCO3 and extracted with EtOAc (2×). The combined organic layers were dried and concentrated to give the 1.53 g (99%) of the title compound. MS (ESI): exact mass calcd. for C19H18N2O, 290.14; m/z found, 291.4 [M+H]+. 1H NMR (CDCl3): 8.00-7.98 (m, 2H), 7.45-7.43 (m, 3H), 7.32-7.28 (m, 4H), 7.23-7.20 (m, 1H), 4.74 (d, J=4.8, 2H), 4.33 (s, 2H), 3.62 (t, J=5.1, 1H), 2.42 (s, 3H).

後処理

  1. additionthe reaction was diluted with satd
  2. extractionaq. NaHCO3 and extracted with EtOAc (2×)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-7b07829790494cbb8674b97951f178ce
出典データセット
uspto-grants-2013_12
特許番号
US08618288B2

反応ノート

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