Triethylamine → HCID 25183073、化合物

HRID 1946681ノート

反応式

HRID 1946681 の反応式
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=C(C(OC)=O)C=C(NCC2CCCC2)N=1.[NH2:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][OH:45])=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:39][C:40]3[CH:47]=[CH:46][C:43]([CH2:44][OH:45])=[CH:42][CH:41]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 693314-Aminobenzyl alcoholHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2 回HCID 86644304HCID 86644304、化合物

生成物 1

HCID 25183073HCID 25183073、化合物収率 72%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 6-(cyclohexyl-cyclopropylmethyl-amino)-pyrimidine-4-carboxylic acid (Intermediate 13, 1.00 g; 3.63 mmol) in dry DMF (100 ml) was treated with polymer-supported Mukaiyama reagent, prepared as described in “S. Crosignani et al. Org. Lett. 2004, 6(24), 4579-4582” (2 987 mg; 6.54 mmol), 4-aminobenzyl alcohol (Fluka, 492 mg; 3.99 mmol) and triethylamine (1.52 ml; 10.9 mmol). The reaction mixture was then stirred at room temperature for 18 hours. DCM was added and the product was filtered through an SPE column (Isolute NH2, 10 g) and the column washed with DCM. The mixture was concentrated then rediluted in AcOEt. The organic phase was washed 5 times with brine, dried over MgSO4 and the solvent removed under vacuum to give the title compound (990 mg, 72%).

後処理

  1. customprepared
  2. filtrationthe product was filtered through an SPE column (Isolute NH2, 10 g)
  3. washthe column washed with DCM
  4. concentrationThe mixture was concentrated
  5. additionthen rediluted in AcOEt
  6. washThe organic phase was washed 5 times with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-8af2e2d7fb244f2faf0994e5cc97178b
出典データセット
uspto-grants-2013_03
特許番号
US08399448B2

反応ノート

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