4-Amino-6-methyl-2-morpholin-4-yl-5-nitropyrimidine → N5-(4-Iodo-2-methoxy-pyridin-3-ylmethylene)-6-methyl-2-morpholin-4-yl-pyrimidine-4,5-diamine

HRID 2377768

반응식

HRID 2377768 반응식
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([CH3:11])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.[H][H].[I:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[C:22]=1[CH:29]=O>[Pd].CO>[I:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[C:22]=1[CH:29]=[N:8][C:7]1[C:2]([NH2:1])=[N:3][C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:5][C:6]=1[CH3:11]

참가 물질

6

반응물 3

HCID 29121954-Amino-6-methyl-2-morpholin-4-yl-5-nitropyrimidineHCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 58819980N5-(4-Iodo-2-methoxy-pyridin-3-ylmethylene)-6-methyl-2-morpholin-4-yl-pyrimidine-4,5-diamine수율 87.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매3회

실험 절차

To 4-amino-6-methyl-2-morpholin-4-yl-5nitropyrimidine (500 mg, 2.09 mmol) and 10% palladium on carbon (100 mg) were added methanol (10 mL) under nitrogen. The reaction mixture was stirred under hydrogen atmosphere (hydrogen balloon) for 22 hours. The solution was filtered through a pad of celite and the filtercake was washed with a small amount of MeOH. The product in MeOH was used for the next step without purification; LCMS (+ESI, M+H+) m/z 210; HPLC: 97% (220 nm). To the crude diamino in MeOH (50 mL) was added a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (604 mg, 2.30 mmol) in MeOH (10 mL) at 0° C. and stirred for 0.5 hour. The resulting mixture was allowed to warm to ambient temperature and stirred for 6 days in an open system exposed to air. The reaction mixture was cooled to 0° C. to afford a crystalline yellow solid, which was collected by filtration to give the title compound (830 mg, 87%): 1H NMR (400 MHz, DMSO) δ 8.43 (s, 1H), 7.85 and 7.62 (d, J=5.3, 1H), 6.23 (br s, 2H), 3.91 (s, 3H), 3.61 (s, 8H), 2.26 (s, 3H); LCMS (+ESI, M+H+) m/z 455.

후처리

  1. filtrationThe solution was filtered through a pad of celite
  2. washthe filtercake was washed with a small amount of MeOH
  3. customThe product in MeOH was used for the next step without purification
  4. stirringstirred for 6 days in an open system
  5. temperatureThe reaction mixture was cooled to 0° C.
  6. customto afford a crystalline yellow solid, which
  7. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-e58fca3901754cc1ae9bf0da7ee507ec
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470696B2

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