Potassium Carbonate → HCID 86670105, 화합물

HRID 1631719노트

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HRID 1631719 반응식
Br[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH2:18][CH:17]3[CH2:19][O:20][CH2:21][CH2:22][N:16]3[C:15]3[N:14]=[C:13]([Cl:23])[N:12]=[CH:11][C:10]2=3)[CH:5]=[CH:4][CH:3]=1.[C:24]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:23][C:13]1[N:12]=[CH:11][C:10]2[N:9]([CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:24])[N:7]=3)[CH2:18][CH:17]3[CH2:19][O:20][CH2:21][CH2:22][N:16]3[C:15]=2[N:14]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 866701045-((6-Bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

생성물 1

HCID 86670105HCID 86670105, 화합물수율 57.4%

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a 10 mL vial was added 5-((6-bromopyridin-2-yl)methyl)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x27, 75 mg, 0.189 mmol), K2CO3 (52.3 mg, 0.378 mmol), PdCl2(dppf) (13.83 mg, 0.019 mmol) and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.053 mL, 0.378 mmol) in dioxane (2 mL) and H2O (0.4 mL) to give an orange suspension. The reaction vial was sealed, heated to 100° C., and stirred overnight. The reaction mixture was then diluted with ethyl acetate and washed with aqueous saturated NH4Cl (3×10 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give crude product, which was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetate/hexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow solid (36 mg, 57%). 1H NMR (400 MHz, DMSO-d6) δ 2.45 (s, 3H), 2.92-3.05 (m, 1H), 3.12-3.27 (m, 2H), 3.40-3.52 (m, 2H), 3.61-3.74 (m, 1H), 3.85-4.00 (m, 2H), 4.18-4.28 (m, 1H), 4.35-4.58 (m, 2H), 7.10-7.17 (m, 2H), 7.30 (s, 1H), 7.60-7.68 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C16H18ClN5O, 331.12. found 331.2.

후처리

  1. customto give an orange suspension
  2. customThe reaction
  3. customvial was sealed
  4. washwashed with aqueous saturated NH4Cl (3×10 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give crude product, which
  9. washeluted
  10. customThe product was collected
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4a2d3c7e61ae4437b098ef36d1080e6d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791107B2

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