Water → 4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

HRID 2114608노트

반응식

HRID 2114608 반응식
I[C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:3]=1.[OH2:17].[C]=O.CN([CH:23]=[O:24])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:11][C:9]1[C:10]2[C:2]([C:23]([OH:24])=[O:17])=[CH:3][N:4]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:5]=2[N:6]=[CH:7][N:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 195974344-Chloro-7-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidineHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 717441504-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

Starting material (1B, 10 g, 29 mmole) was taken in 500 mL DMF and 100 mL H2O together with palladium acetate (0.32 g, 1.4 mmole). The reaction mixture was stirred in a pressure reactor at 50° C. under 100 psi carbon monoxide for 6.5 h and room temperature for 16 h. The reaction mixture was then concentrated and residue triturated with 100 mL of 1:1 EtOAc/Ch2Cl2 followed by 50 mL CH2Cl2, The solid was collected after filtration and dried over P2O5 to furnish 21 g of an off-white solid. This solid was then triturated with a mixture of formic acid/H2O (21 mL/5 mL). The solid collected after filtration and drying over P2O5 furnished 6.5 g of 1 C (m/z 265.1, retention time 2.5 min. with HPLC method 1).

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. customresidue triturated with 100 mL of 1:1 EtOAc/Ch2Cl2
  3. customThe solid was collected
  4. filtrationafter filtration
  5. dry with materialdried over P2O5

출처 및 근거

ORD 기록
ord-4d0403a8acca4df5a79722a04a2776f8
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07435739B2

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