Sulfamic Acid → 6-(2,6-dichlorophenyl)-2-N-[4-(diethylamino)butyl]pyrido[2,3-d]pyrimidine-2,7-diamine

HRID 3438

반응식

HRID 3438 반응식
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH2:20])=[N:8][C:6]=2[N:7]=1.S(=O)(=O)(O)N.[CH2:26]([N:28]([CH2:31][CH2:32][CH2:33][CH2:34]N)[CH2:29][CH3:30])[CH3:27]>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[C:9]([NH2:20])=[N:8][C:6]2[N:7]=[C:2]([NH:1][CH2:34][CH2:33][CH2:32][CH2:31][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[N:3]=[CH:4][C:5]=2[CH:11]=1

참가 물질

4

반응물 3

HCID 5987Sulfamic AcidHCID 117976N,N-Diethyl-1,4-butanediamineHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

생성물 1

HCID 53281336-(2,6-dichlorophenyl)-2-N-[4-(diethylamino)butyl]pyrido[2,3-d]pyrimidine-2,7-diamine

반응 조건

온도
150 °C

실험 절차

A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (40 g) from Example 1, sulfamic acid (25.4 g) and diethylaminobutylamine (205 mL) was heated to approximately 150° C. for 28 hours. The reaction temperature was lowered to 50° C., and excess diethylaminobutylamine was removed in vacuo. After cooling to 25° C., the residue was suspended in water. The aqueous solution was made alkaline with a solution of saturated sodium bicarbonate and extracted with dichloromethane several times. The dichloromethane layers were combined, washed several times, first with a saturated solution of sodium bicarbonate then a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was washed repeatedly with diethyl ether and then crystallized from ethyl acetate. The recrystallized product was further purified by column chromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (85:14:1) followed by ethyl acetate:ethyl alcohol:triethylamine (9:2:1) to afford 36.2 g of the title compound 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% NH3 in CH4): 461=M+ +C2H5, 433=M+ +H (Base), 417, 403, 360.

후처리

  1. customwas lowered to 50° C.
  2. customexcess diethylaminobutylamine was removed in vacuo
  3. temperatureAfter cooling to 25° C.
  4. extractionextracted with dichloromethane several times
  5. washwashed several times
  6. dry with materialfirst with a saturated solution of sodium bicarbonate then a saturated solution of sodium chloride, dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed repeatedly with diethyl ether
  9. customcrystallized from ethyl acetate
  10. customThe recrystallized product was further purified by column chromatography
  11. washeluting first with ethyl acetate:methyl alcohol:triethylamine (85:14:1)

출처 및 근거

ORD 기록
ord-c0e5a6c6eb1740d4b28e4ccae931db8f
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733913

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