4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
Synonym(s):4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
- CAS NO.:3680-69-1
- Empirical Formula: C6H4ClN3
- Molecular Weight: 153.57
- MDL number: MFCD01686865
- EINECS: 628-079-2
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-24 18:18:52
What is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine?
The Uses of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine is used in the manufacture of Tofacitinib citrate.
Synthesis
A mixture of compound 6-Chloro-5-(prop-2-en-1-yl)pyrimidin-4-amine (68 g, 0.41 mol), Et3N (60.9 g, 0.6 mol), and DMSO (47 g, 0.6 mol) in MeOH (320 ml) was cooled to –5–0°C and ozone was bubbled through the mixture for 2 h. After nitrogen was bubbled through the mixture to remove the excess of ozone, thiocarbamide (61.2 g, 0.81 mol) was added and mixture stirred for 1 h, until the starch-KI paper did not turn blue. Then AcOH (120 g, 2 mol) was added and stirring at room temperature continued for 14 h. The solvent was removed under reduced pressure. The residue was extracted with EtOAc (500 ml), washed with brine (2×200 ml) and aqueous NaHCO3 to neutralize the residual AcOH. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine, that was recrystallized from a mixture of petroleum ether – EtOAc, 2:1. Yield 26.1 g (43%), white solid.
Properties of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
Melting point: | 188-194 °C |
Boiling point: | 289.2±50.0 °C(Predicted) |
Density | 1.61±0.1 g/cm3(Predicted) |
storage temp. | Keep in dark place,Inert atmosphere,2-8°C |
solubility | Soluble in DMSO, ethyl acetate and methanol. |
form | Crystalline Powder |
color | White to tan |
Safety information for 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral |
Precautionary Statement Codes |
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
Computed Descriptors for 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
InChIKey | BPTCCCTWWAUJRK-UHFFFAOYSA-N |
Abamectin manufacturer
EPOCH LABS
ALTRAKEM PHARMA LIFE SCIENCES PRIVATE LIMITED
VGS SYNTHESIS PRIVATE LIMITED
A.R. LIFE SCIENCES PVT. LTD.
GOALSY PHARMA
Bulat Pharmaceutical Pvt Ltd
REAX CHEMICALS
Credas Labs Pvt Ltd
PRODIGIOUS LIFE SCIENCES
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