HCID 67328269、化合物 → HCID 53373261、化合物

HRID 1846177ノート

反応式

HRID 1846177 の反応式
C([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27]COC)=[N:11][C:12]([NH2:16])=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[NH2:16][C:12]1[N:11]=[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=1

参加物

5

反応物 1

HCID 67328269HCID 67328269、化合物

生成物 1

HCID 53373261HCID 53373261、化合物

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

To a stirred solution containing 133 mg (0.48 mmol) of 5-(benzyloxy)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidin-2-amine in 10 mL of methanol were added two drops of concentrated HCl and the mixture was stirred at reflux for 16 h. To the mixture were added 10 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (13×3 cm). Elution with 17:3 dichloromethane-methanol afforded the expected product as white solid: yield 68 mg (69%); mp: 103-104° C.; silica gel TLC Rf 0.20 (17:3 dichloromethane-methanol); 1H NMR (methanol-d4) δ 1.29-1.35 (m, 12H), 1.50 (quint, 2H, J=6.8 Hz), 1.64 (quint, 2H, J=7.6 Hz), 2.37 (s, 3H), 2.71 (dd, 2H, J=7.6, 7.6 Hz) and 3.51 (t, 2H, J=6.4); 13C NMR (methanol-d4) δ 16.42, 25.50, 27.07, 29.00, 29.02, 29.08, 29.13, 29.25, 30.72, 32.22, 61.56, 138.97, 153.46, 157.60 and 160.84; mass spectrum (APCI+), m/z 282.2170 (M+H) (C15H28N3O2 requires 282.2182).

後処理

  1. temperatureat reflux for 16 h
  2. stirringThe reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrated was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column (13×3 cm)
  6. washElution with 17:3 dichloromethane-methanol

出典と根拠

ORDレコード
ord-22e1a813c20d4290a8bb8a11dfcca3a0
出典データセット
uspto-grants-2015_02
特許番号
US08952025B2

反応ノート

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