Phosphorus oxychloride → 4-chloro-N-(1-methyl-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 577701Notes

Reaction equation

HRID 577701 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:9]=[C:10](O)[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:4]=[N:3]1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:10]1[C:11]2[CH:16]=[CH:15][NH:14][C:12]=2[N:13]=[C:8]([NH:7][C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178480794HCID 178480794, compound

Product 1

HCID 866796464-chloro-N-(1-methyl-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amineYield 56%

Procedure

A solution of 2-((1-methyl-1H-pyrazol-4-yl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-ol (5 g, 0.02 mol) in POCl3 (50 mL) was stirred at 120° C. for 4 hrs. After removal of POCl3 by rotary evaporation, water (37 mL) was added. The pH was adjusted to 10 by aq. NaOH (2 mol/L, 30 mL) and then extracted with EtOAc/THF (2:1, three×200 mL). The combined organic layers were concentrated to dryness to afford the title compound (2.8 g, 56% yield) as a brown solid, which was used as is in the next step.

Workup

  1. customAfter removal of POCl3
  2. customby rotary evaporation, water (37 mL)
  3. additionwas added
  4. extractionextracted with EtOAc/THF (2:1, three×200 mL)
  5. concentrationThe combined organic layers were concentrated to dryness

Sources & evidence

ORD record
ord-4294898f8a49420ba0c5897e0975ba71
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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