3-Chlorobenzoic Acid → HCID 178478055, compound

HRID 1747674Notes

Reaction equation

HRID 1747674 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=O.P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:9]=[C:14]([C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([Cl:10])[CH:12]=1)[NH:8]2

Participants

4

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 24813Phosphorus oxychlorideHCID 780104,5-Pyrimidinediamine, 6-chloro-

Product 1

HCID 178478055HCID 178478055, compoundYield 99.8%

Conditions

Temperature
100 °C

Procedure

To a mixture of 6-Chloro-4,5-diaminopyrimidine (0.70 g, 4.84 mmol) and 3-chlorobenzoic acid (0.76 g, 4.84 mmol) in the flask was added phosphoryl chloride (40.0 mL), and the resulting mixture was stirred for 16 h at 100° C. The reaction mixture was evaporated to remove excess phosphoryl chloride, and the residue was added to water (20 mL). The precipitate was filtered and purified by flash chromatography (0 to 5% Methanol/DCM) to afford the title compound (1.28 g, 31%) as a yellow solid. LC/MS: Rt=1.59 min, ES+ 265.0 (FA standard).

Workup

  1. customThe reaction mixture was evaporated
  2. customto remove excess phosphoryl chloride
  3. additionthe residue was added to water (20 mL)
  4. filtrationThe precipitate was filtered
  5. custompurified by flash chromatography (0 to 5% Methanol/DCM)

Sources & evidence

ORD record
ord-3bf007ba8a8e4af39caa603ce1d0f598
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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