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Home > Encyclopedia > 4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine structure

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine 

structure
  • CAS No:

    71149-52-5

  • Formula:

    C7H6ClN3

  • Chemical Name:

    4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine

  • Synonyms:

    1H-Pyrrolo[2,3-d]pyrimidine, 4-chloro-2-methyl-;4-chloro-2-methyl-7H-pyrrolo[2,3-d]pyrimidine;2-methyl-4-chloro-pyrrolopyrimidine;4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine;4-Chloro-2-methyl-7H-pyrrolo

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine Basic Attributes

167.6

167.025024

DTXSID70448334

2933990090

Characteristics

41.6

2

1.4±0.1 g/cm3

207-208 °C

229.938ºC at 760 mmHg

114.932ºC

1.688

Safety Information

Ⅲ

6.1

2811

3

36

26

4-Chloro-2-methyl-1H-pyrrolo[2,3-d]pyrimidine Use and Manufacturing

A suspension of 90 mg (0.60 mmol) of the above hydroxypyrrolopyrimidine in 2 mL of phosphorous oxychloride was refluxed for 2 hours. The excess phosphorous oxychloride was removed and the residue was quenched carefully with ice. The mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over MgSO2-Methyl-3H-pyrrolo[2, 3-d]pyrimidin-4(7H)-one 23-a (10.54 g, 70.6 mmol) was dissolved in Toluene (20 mL) under inert atmosphere. DIPEA (24 mL, 141 mmol, 2 eq.) and POC13 (19.5 mL, 212 mmol, 3 eq.) were added dropwise at 70°C and the mixture was then heated to 106°C. After 16 hours, the solution was concentrated in vacuo, extracted with ethyl acetate and washed with saturated NaHCO3 solution. Thecombined organic layers were dried over Na2504, and concentrated in vacuo to yield a grey oil which was suspended in water/heptanes to afford a white solid intermediate 23(5.9 g, 50percent).N-(4-methoxyphenyl)-N, 2-dimethyl-7H-pyrrolo[2, 3-d]pyrimidin-4-amine (AAG20); Compound 4 (0.005 mol, 0.835 g) was added to a solution of 4-methoxy-N-methylaniline (5, 0.006 mol, 0.822 g) in i-propanol (10 ml) with drops of conc. HCl. The resulting solution was transferred to a microwave vial (20 ml) and irradiated at 110° C. After 6 h, the reaction was completed and AAG20 was obtained after the chromatographic purification as a white solid (1.01 g) with 80percent yield. TLC RTo a solution of

Computed Properties

Molecular Weight:167.59
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:167.0250249
Monoisotopic Mass:167.0250249
Topological Polar Surface Area:41.6
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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