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Ammonium formate → 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

HRID 1966739
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HRID 1966739 반응식
[C:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:13]([O:19][CH3:20])=[N:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:8][C:7]=1[N+:21]([O-])=O)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Zn]>[NH2:18][C:15]1[N:14]=[C:13]([O:19][CH3:20])[C:12]([C:9]2[CH:8]=[C:7]([NH2:21])[C:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:11][CH:10]=2)=[CH:17][N:16]=1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 585420425-(4-Tert-butylamino-3-nitro-phenyl)-4-methoxy-pyrimidin-2-ylamine

생성물 1

HCID 585420094-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine수율 87%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

To a round bottom flask is added 5-(4-tert-Butylamino-3-nitro-phenyl)-4-methoxy-pyrimidin-2-ylamine (150 mg, 0.473 mmol) in MeOH (5 mL), followed by the addition of ammonium formate (268 mg, 4.25 mmol) and of zinc dust (154 mg, 2.37 mmol). The reaction mixture is stirred at 50° C. for 1 hour. The reaction mixture is filtered through diatomaceous earth, washing with MeOH. The filtrate is concentrated in vacuo. The residue is diluted with EtOAc, washed with water, dried with Na2SO4, filtered and concentrated to afford 4-(2-amino-4-methoxy-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (118 mg, 87%) as a light brown solid. LCMS (ESMS): m/z 288.48 (M++1)

후처리

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. washwashing with MeOH
  3. concentrationThe filtrate is concentrated in vacuo
  4. additionThe residue is diluted with EtOAc
  5. washwashed with water
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e7e190335a054abbbc24c60c97c356a6
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08420655B2

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