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

HRID 1966739Notes

Reaction equation

HRID 1966739 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-e7e190335a054abbbc24c60c97c356a6
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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