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Potassium Carbonate → 5-[3'-Amino-6-ethoxy-2-(2,2,2-trifluoro-ethoxy)-biphenyl-4-ylmethyl]-pyrimidine-2,4-diamine

HRID 2416311
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HRID 2416311 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([OH:26])=[CH:10][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:12][C:13]=2[O:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:38][C:39]([F:42])([F:41])[F:40])(=O)=O>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:10][C:9]=2[O:26][CH2:38][C:39]([F:42])([F:41])[F:40])[CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 5565652,2,2-Trifluoroethyl Methanesulfonate2회HCID 226369793'-Amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-ol

생성물 1

HCID 226369015-[3'-Amino-6-ethoxy-2-(2,2,2-trifluoro-ethoxy)-biphenyl-4-ylmethyl]-pyrimidine-2,4-diamine

시약·촉매·용매 1

HCID 6342Acetonitrile
용매

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온도
100 °C

실험 절차

3′-Amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-ol (527 mg; 1.5 mmol) is suspended in acetonitrile (60 ml; dried over a molecular sieve), potassium carbonate (621 mg; 4.5 mmol) is added and the mixture is heated to a bath temperature of 100° C. 2,2,2-Trifluoroethyl methanesulphonate (0.353 ml; 3.0 mmol) is added and the mixture is boiled under reflux for 3 hours. After this period of time, potassium carbonate (414 mg; 3 mmol) and 2,2,2-trifluoroethyl methanesulphonate (0.353 ml; 3.0 mmol) are again added and the mixture is stirred under reflux for a further 2 hours. The same procedure is repeated four more times at intervals of two hours. The suspension is then filtered with suction and the filtrate is concentrated. The residue is chromatographed over silica gel (120 g) with methylene chloride/methanol/NH4OH (1/1 mixture of 90/10/1 and 19/1/0.05).

후처리

  1. additionis added
  2. temperatureunder reflux for 3 hours
  3. temperatureunder reflux for a further 2 hours
  4. customat intervals of two hours
  5. filtrationThe suspension is then filtered with suction
  6. concentrationthe filtrate is concentrated
  7. customThe residue is chromatographed over silica gel (120 g) with methylene chloride/methanol/NH4OH (1/1 mixture of 90/10/1 and 19/1/0.05)

출처 및 근거

ORD 기록
ord-c12e582754a0450aaaf69a064ea15210
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06821980B1

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