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

HRID 2189315노트

반응식

HRID 2189315 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e5c17bd07e9844ec96dde42f1cab072d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324225B2

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