Sulfuric Acid → Methyl 3-(5-aminopyrimidin-2-yl)benzoate

HRID 655336Notes

Reaction equation

HRID 655336 reaction equation
CN(C=[N:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[N:10][CH:11]=1)C.S(=O)(=O)(O)O>CO>[NH2:5][C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[N:8][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 594848583-[5-(((Dimethylamino)methylene)amino)pyrimidin-2-yl]benzoic acid methyl ester

Product 1

HCID 59484836Methyl 3-(5-aminopyrimidin-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
7.5 °C

Procedure

10.2 g (35.9 mmol) of methyl 3-[5-(dimethylaminomethyleneamino)pyrimidin-2-yl]benzoate are suspended in 1 l of methanol. 5.3 ml (107.3 mmol) of fuming sulfuric acid are added dropwise with gentle cooling (about 5-10° C.) (note, strongly exothermic reaction). When the addition is complete, the mixture is stirred firstly at room temperature for 30 min and subsequently at an oil-bath temperature of 88°. The reaction is monitored by means of HPLC. After 20 h, the clear, dark-yellow solution is evaporated to dryness. The residue is dissolved in 600 ml of ethyl acetate and washed with 2×150 ml of 1 N NaOH and 2×1 N HCl, dried over sodium sulfate and evaporated; yield: 3 g; HPLC: Rt=2.17 min (method B); LC-MS: 300 (M+H).

Workup

  1. customnote, strongly exothermic reaction)
  2. additionWhen the addition
  3. waitAfter 20 h
  4. customthe clear, dark-yellow solution is evaporated to dryness
  5. dissolutionThe residue is dissolved in 600 ml of ethyl acetate
  6. washwashed with 2×150 ml of 1 N NaOH and 2×1 N HCl
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-3752723ef7504f738705f8f67fdb9456
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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