Sodium Carbonate → N-[3-(2-aminopyridin-4-yl)-5-methylphenyl]-4-methoxypyrimidin-2-amine

HRID 2207361노트

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HRID 2207361 반응식
Br[C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH2:18][C:19]1[CH:24]=[C:23](B(O)O)[CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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].C(Cl)Cl>[NH2:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[C:4]([NH:9][C:10]3[N:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH:22]=[CH:21][N:20]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 23546911B-(2-Amino-4-pyridinyl)boronic acidHCID 67250894N-(3-bromo-5-methylphenyl)-4-methoxypyrimidin-2-amine

생성물 1

HCID 118103324N-[3-(2-aminopyridin-4-yl)-5-methylphenyl]-4-methoxypyrimidin-2-amine

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of N-(3-bromo-5-methylphenyl)-4-methoxypyrimidin-2-amine (125 mg, 0.425 mmol), 2-aminopyridine-4-boronic acid (103 mg, 0.467 mmol), PdCl2(dppf)-CH2Cl2 adduct (35 mg, 0.042 mmol) and sodium carbonate (425 μL, 0.850 mmol) in dioxane (3 mL) was heated to 100° C. for 14 hours. The reaction mixture was filtered through a CELITE pad and washed with dioxane (3×). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (methanol/ethyl acetate) to give N-[3-(2-aminopyridin-4-yl)-5-methylphenyl]-4-methoxypyrimidin-2-amine as a tan solid. MS ESI calc'd for C17H18N5O [M+H]+ 308. found 308. 1H NMR (500 MHz, DMSO-d6) δ 9.59 (s, 1H), 8.20 (d, J=5.7 Hz, 1H), 7.95-7.88 (m, 2H), 7.61 (s, 1H), 7.00 (s, 1H), 6.69 (d, J=5.4 Hz, 1H), 6.64 (s, 1H), 6.28 (d, J=5.6 Hz, 1H), 5.95 (s, 2H), 3.92 (s, 3H), 2.32 (s, 3H).

후처리

  1. filtrationThe reaction mixture was filtered through a CELITE pad
  2. washwashed with dioxane (3×)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (methanol/ethyl acetate)

출처 및 근거

ORD 기록
ord-a63a1c59cfd04c3fafca2d8954708a58
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376418B2

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