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1,3-Benzoxazol-6-amine → N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amine

HRID 1912649
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HRID 1912649 반응식
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[C:27]2[CH:28]=[C:29]([NH2:32])[CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:1]([O:8][C:9]1[C:10]([NH:32][C:29]2[CH:30]=[CH:31][C:26]3[N:25]=[CH:24][O:23][C:27]=3[CH:28]=2)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 5841201,3-Benzoxazol-6-amineHCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidineHCID 178418730sodium 2-methylpropan-2-olate

생성물 1

HCID 66958358N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amine수율 25.9%

시약·촉매·용매 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 1140Toluene용매

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온도
115 °C

실험 절차

5-(benzyloxy)-4-chloro-6-p-tolylpyrimidine (50 mg, 0.161 mmol) was dissolved in PhMe, to this was added benzo[d]oxazol-6-amine (23.7 mg, 1.1 eq), Pd(dba)2 (4.6 mg, 0.05 eq), t-BuONa (31 mg, 2 eq), and (±)-BINAP (15 mg, 0.15 eq). The mixture was degassed and heated at 115° C. overnight. The mixture was cooled to room temperature, diluted with EtOAc and washed with H2O. Preparative TLC gave 17 mg of the title compound.

후처리

  1. customThe mixture was degassed
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with EtOAc
  4. washwashed with H2O

출처 및 근거

ORD 기록
ord-72bc7667b5d54a25b34032e2f8cef03b
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609676B2

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