Anthranilic Acid → HCID 69510256, compound

HRID 969702Notes

Reaction equation

HRID 969702 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9](=O)[CH3:10])[CH:6]=[CH:5][N:4]=1.[C:12]([OH:21])(=[O:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:15].CC1C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([CH:9]([NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]([OH:21])=[O:20])[CH3:10])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 21615194HCID 21615194, compound

Product 1

HCID 69510256HCID 69510256, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(2-methylamino-pyrimidin-4-yl)-ethanone (Step A, 1.0 g, 6.61 mmol) in dry toluene (40 mL) was added anthranilic acid (635 mg, 4.63 mmol) and TsOH (25 mg, 0.132 mmol). The resulting mixture was heated at 90° C. for 20 h, then cooled to RT. NaBH4 (500 mg, 13.23 mmol) was added and the reaction was stirred for 5 h. The reaction was quenched with MeOH and evaporated in vacuo. The crude solid was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (95:5) gave final compound. MS m/z: 273.3 (M+H). Calc'd. for C14H17N4O2-273.3.

Workup

  1. temperaturecooled to RT
  2. customThe reaction was quenched with MeOH
  3. customevaporated in vacuo
  4. customThe crude solid was purified by chromatography on silica gel
  5. washElution with CH2Cl2

Sources & evidence

ORD record
ord-aadf93fd736241d3a12e8aa48b1029f7
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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