Triethylamine → Pyrido[2,3-d]pyrimidin-7-one deriv. 13

HRID 3232

반응식

HRID 3232 반응식
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[NH:10][C:8]=2[N:9]=1.C(N(CC)CC)C.Cl.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37]Cl)=[CH:33][CH:32]=1.[Na]>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11](=[O:22])[N:10]([CH2:37][C:34]3[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=3)[C:8]=2[N:9]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 5360545SodiumHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol2회

생성물 1

HCID 5328633Pyrido[2,3-d]pyrimidin-7-one deriv. 13

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
70 °C

실험 절차

To a suspension of NaH (60% in mineral oil, 32 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (200 mg, 0.65 mmol) and the mixture heated to 70° C. In a second flask containing triethyl amine (220 μL, 1.59 mmol) in 4 mL of dimethylformamide was added 4-picolyl chloride hydrochloride (137 mg, 0.84 mmol). This dark red mixture was added to the above solution of the sodium salt of 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one. The mixture was heated to 70° C., then cooled to room temperature. The mixture was poured into 20 mL of ice water, and the resulting precipitate was removed by filtration and washed with water. This solid was washed with 10% methanol in ethyl acetate to provide 96 mg of crude product. The filtrate was concentrated to provide an additional 77 mg of crude product. An analytical sample was obtained by purification by flash chromatography, eluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate to provide 2-amino-6-(2,6-dichlorophenyl)-8-pyridin-4-ylmethyl-8H-pyrido[2,3-d]pyrimidin-7-one; mp 268°-270° C. dec.

후처리

  1. temperatureThe mixture was heated to 70° C.
  2. temperaturecooled to room temperature
  3. customthe resulting precipitate was removed by filtration
  4. washwashed with water
  5. washThis solid was washed with 10% methanol in ethyl acetate
  6. customto provide 96 mg of crude product
  7. concentrationThe filtrate was concentrated
  8. customto provide an additional 77 mg of crude product
  9. customAn analytical sample was obtained by purification by flash chromatography
  10. washeluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-d68719fd07424782a508df3f799b02af
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733914

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