Trifluoroacetic acid → ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882128노트

반응식

HRID 882128 반응식
[C:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(OCC)(=O)C>[C:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:15]3[C:16]4[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][NH:21][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][N:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 89630128Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

생성물 1

HCID 89629984ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (17 mg, 0.035 mmol) was treated with TFA (500 μL) and stirred at room temperature for 1 hour. To the resulting mixture was added 1 N sodium hydroxide solution (1 mL) and ethyl acetate (3 mL), then allowed to keep stirring for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (×3). The combined organic layers were concentrated under reduced pressure and then purified by chromatography on silica eluting with 60-80% ethyl acetatehexane to give ethyl 4-(3-(2-cyanopyrimidin-4-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate. LRMS (ESI) calc'd for C20H15N6O2[M+H]+: 371, found 371. 1H NMR (600 MHz, DMSO-D6) δ 13.04 (bs, 1H), 9.07 (d, J=5.28 Hz, 1H), 8.97 (s, 1H), 8.49 (m, 2H), 8.38 (m, 2H), 7.91 (d, J=7.63 Hz, 1H), 7.72 (t, J 7.63 Hz, 1H), 3.84 (q, J=7.04 Hz, 2H), 0.84 (t, J=7.04 Hz, 3H).

후처리

  1. stirringto keep stirring for 30 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (×3)
  4. concentrationThe combined organic layers were concentrated under reduced pressure
  5. custompurified by chromatography on silica eluting with 60-80% ethyl acetatehexane

출처 및 근거

ORD 기록
ord-c71d2cf5723f4fa68e76fe4da8a9e920
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993756B2

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