Dimethylamine → 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

HRID 2189315ノート

反応式

HRID 2189315 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([OH:13])=O)[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:37]([CH3:39])[CH3:38])C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.CNC>CN(C=O)C.C1COCC1>[CH3:38][N:37]([CH3:39])[C:11]([C:9]1[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[CH:4][C:5]=2[CH:10]=1)=[O:13]

参加物

7

反応物 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 735546592-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

生成物 1

HCID 866373462-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide収率 72.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid (80 mg, 0.30 mmol), BOP (159 mg, 0.36 mmol) and N,N-diisopropylethylamine (0.078 mL, 0.45 mmol) in DMF (3 mL) is added 0.164 mL of 2 N dimethylamine in THF solution at room temperature. The mixture is stirred at room temperature for 3 h, quenched with 1N NaOH aqueous solution, and extracted with EtOAc. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, 5% MeOH in CH2Cl2) to give 64 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide.

後処理

  1. customquenched with 1N NaOH aqueous solution
  2. extractionextracted with EtOAc
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by column chromatography (SiO2, 5% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-e5c17bd07e9844ec96dde42f1cab072d
出典データセット
uspto-grants-2012_12
特許番号
US08324225B2

反応ノート

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