Triethylamine → (+/-)-Methanesulfonic acid (2-{3-[8-(3-cyano-phenyl)-6-(4-methoxy-phenyl)-5-methyl-7-oxo-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-ylamino]-phenyl}-ethyl)-ester

HRID 1247644노트

반응식

HRID 1247644 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[N:16]=[C:15]3[N:17]([C:31]4[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=4)[C:34]#[N:35])[C:18](=[O:30])[N:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH:20]([CH3:21])[C:14]3=[CH:13][N:12]=2)[CH:7]=[CH:8][CH:9]=1.C(N(CC)CC)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl>[C:34]([C:33]1[CH:32]=[C:31]([N:17]2[C:15]3[N:16]=[C:11]([NH:10][C:6]4[CH:5]=[C:4]([CH2:3][CH2:2][O:1][S:47]([CH3:46])(=[O:49])=[O:48])[CH:9]=[CH:8][CH:7]=4)[N:12]=[CH:13][C:14]=3[CH:20]([CH3:21])[N:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:18]2=[O:30])[CH:38]=[CH:37][CH:36]=1)#[N:35]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 9870839(+/-)-3-[7-[3-(2-hydroxy-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

생성물 1

HCID 10325979(+/-)-Methanesulfonic acid (2-{3-[8-(3-cyano-phenyl)-6-(4-methoxy-phenyl)-5-methyl-7-oxo-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-ylamino]-phenyl}-ethyl)-ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(±)-3-[7-[3-(2-Hydroxy-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.67 mg; 1.27 mmol) (from Example 4 supra) was suspended in dichloromethane (13 mL). The mixture was treated with triethylamine (0.23 mL; 1.65 mmol) and methane-sulfonyl chloride (0.13 mL; 1.68 mmol) (Aldrich). The solid went into solution as the methanesulfonyl chloride was added. After 45 minutes, the reaction was shown by thin layer chromatography to be complete. The reaction was diluted with additional dichloromethane and washed with water and then brine. The organic phase was dried over anhydrous sodium sulfate, concentrated and dried under high vacuum to give crude (±)-methanesulfonic acid (2-{3-[8-(3-cyano-phenyl)-6-(4-methoxy-phenyl)-5-methyl-7-oxo-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-ylamino]-phenyl}-ethyl)-ester as a foam. This material was used in the next step without further purification. (Yield: 0.76 g, 95.4%).

후처리

  1. additionwas added
  2. washwashed with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customdried under high vacuum

출처 및 근거

ORD 기록
ord-17b2dcb2cadb46ef8e160150f33a83d2
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129351B2

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