Sodium 2-methylbutan-2-olate → Tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate

HRID 886806

반응식

HRID 886806 반응식
[NH2:1][C:2]1[N:3]=[C:4]([CH3:20])[C:5]2[CH:11]=[C:10]([C:12]3[S:13][CH:14]=[CH:15][N:16]=3)[C:9](=[O:17])[N:8]([CH2:18][CH3:19])[C:6]=2[N:7]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:39]=[CH:38][C:37](I)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].CCC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC(O)=O.CC(P(C(C)(C)C)C1C(C2[C-]=CC=CC=2)=CC=CC=1)(C)C.[Pd]>[CH2:18]([N:8]1[C:6]2[N:7]=[C:2]([NH:1][C:37]3[CH:36]=[CH:35][C:34]([N:31]4[CH2:30][CH2:29][N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[CH2:33][CH2:32]4)=[CH:39][CH:38]=3)[N:3]=[C:4]([CH3:20])[C:5]=2[CH:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][N:16]=2)[C:9]1=[O:17])[CH3:19]

참가 물질

6

반응물 3

HCID 2733478Sodium 2-methylbutan-2-olateHCID 2795511Tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylateHCID 161233812-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one

생성물 1

HCID 57606982Tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate수율 36.9%

시약·촉매·용매 2

HCID 119822622-(2'-Di-tert-butylphosphine)biphenylpalladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

Acetato(2′-di-t-butylphosphino-1,1′-biphenyl-2-yl)palladium(II) (45 mg, 0.098 mmol) was added to pressure tube charged with 2-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (141 mg, 0.490 mmol), tert-butyl-4-(4-iodophenyl)tetrahydro-1(2H)pyrazinecarboxylate (209 mg, 0.539 mmol), and sodium tert-pentoxide (135 mg, 1.23 mmol) in dry toluene (1.5 mL). The pressure was capped under nitrogen and heated to 70° C.). After 60 hours, the reaction was cooled to room temperature and filtered through a pad of Celite. The filtrate was purified on silica gel (1:1 hexanes:ethyl acetate) to provide the product, tert-butyl 4-(4-(8-ethyl-4-methyl-7-oxo-6-(thiazol-2-yl)-7,8-dihydropyrido[2,3-d]pyrimidin-2-ylamino)phenyl)piperazine-1-carboxylate (99 mg, 34% yield).

후처리

  1. customThe pressure was capped under nitrogen
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered through a pad of Celite
  4. customThe filtrate was purified on silica gel (1:1 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-609acabf051a43289017ec5bcc276045
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247408B2

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