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Ammonium Chloride → 4-[1-(2-aminopyrimidin-4-yl)-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

HRID 1398686
ノート
印刷プレビュー

反応式

HRID 1398686 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([O:11][CH:12]3[CH2:15][O:14][CH2:13]3)[N:8]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=3)[C:7]=2[CH:23]=1)#[CH:2].C([N-]C(C)C)(C)C.[Li+].[N:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[C:38](=[O:40])[CH3:39].[Cl-].[NH4+]>C1COCC1>[NH2:22][C:18]1[N:17]=[C:16]([N:8]2[C:7]3[CH:23]=[C:3]([C:1]#[C:2][C:38]([C:33]4[N:34]=[CH:35][CH:36]=[CH:37][N:32]=4)([OH:40])[CH3:39])[CH:4]=[CH:5][C:6]=3[N:10]=[C:9]2[O:11][CH:12]2[CH2:13][O:14][CH2:15]2)[CH:21]=[CH:20][N:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 116079091-(Pyrimidin-2-yl)ethan-1-oneHCID 866696124-[6-ethynyl-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine

生成物 1

HCID 681817484-[1-(2-aminopyrimidin-4-yl)-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-6-yl]-2-(pyrimidin-2-yl)but-3-yn-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 4-[6-ethynyl-2-(oxetan-3-yloxy)-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine (270 mg, 0.88 mmol) in dry THF (5 mL) at −78° C. was introduced lithium diisopropylamide (1.10 mL of a 2M solution in THF, 2.20 mmol). After 15 minutes, 1-pyrimidin-2-yl-ethanone (107 mg, 0.88 mmol) was added and the reaction mixture maintained at −78° C. for 15 minutes. Following 2 hr at RT, saturated aqueous ammonium chloride (0.5 ml) was added and the solution concentrated in vacuo. The residue was dissolved in DCM (10 mL), washed with water (2 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by column chromatography (Biotage, DCM containing a 0-12% gradient of methanol) furnished the title compound as a yellow solid: 1H NMR (500 MHz, DMSO) delta 1.90 (3H, s), 4.78 (2H, dd, J=7.8, 4.9 Hz), 4.98 (2H, t, J=7.1 Hz), 5.87-5.80 (1H, m), 6.16 (1 H, s), 7.11 (1H, d, J=5.5 Hz), 7.14 (2H, s), 7.25 (1H, dd, J=8.2, 1.2 Hz), 7.45 (1H, d, J=8.2 Hz), 7.52 (1H, t, J=4.8 Hz), 8.16 (1H, s), 8.44 (1H, d, J=5.5 Hz), 8.91 (2H, d, J=4.8 Hz); LC-MS: m/z=+430.05 (M+H)+.

後処理

  1. waitFollowing 2 hr at RT
  2. concentrationthe solution concentrated in vacuo
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. washwashed with water (2 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography (Biotage, DCM containing a 0-12% gradient of methanol)

出典と根拠

ORDレコード
ord-97e5158e5a1047079a15c4f8c35795c9
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901313B2

反応ノート

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