| Identification | More | [Name]
Pyrimidine-5-carboxaldehyde | [CAS]
10070-92-5 | [Synonyms]
5-FORMYLPYRIMIDINE
PYRIMIDINE-5-CARBALDEHYDE
PYRIMIDINE-5-CARBOXALDEHYDE
PYRIMIDINE-5-CARBOXYALDEHYDE
RARECHEM AK ML 0565
5-Pyrimidinecarboxaldehyde (7CI,8CI,9CI)
5-Pyrimidinecarbaldehyde
5-PYRIMIDINECARBOXALDEHYDE
Pyrimidine-5-carboxylaldehyde | [Molecular Formula]
C5H4N2O | [MDL Number]
MFCD03426065 | [Molecular Weight]
108.1 | [MOL File]
10070-92-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
39-43°C | [Boiling point ]
80-82°C 4mm | [density ]
1.23 | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
solid | [pka]
1.15±0.10(Predicted) | [color ]
Light yellow to yellow | [InChI]
InChI=1S/C5H4N2O/c8-3-5-1-6-4-7-2-5/h1-4H | [InChIKey]
FREJAOSUHFGDBW-UHFFFAOYSA-N | [SMILES]
C1=NC=C(C=O)C=N1 | [CAS DataBase Reference]
10070-92-5(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen;Light sensitive;Air sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P305+P351+P338-P405-P501a | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933599590 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Pyrimidine-5-carboxaldehyde is used in the preparation of (S)- and (R)-pyrimidyl alkanol by reacting with diisopropylzinc and (n-butyl)ethyl(n-hexyl)(n-propyl)methane. | [General Description]
Pyrimidine-5-carboxaldehyde serves as a reagent for synthesizing (E)-2-Carbamoyl-1-(naphthalene-2-yl)-3-(pyrimidin-5-yl)prop-2-en-1-one and modifying ring B structures by incorporating different pyridines[6]. The compound reacts with diisopropylzinc under asymmetric autocatalysis to produce optically active pyrimidyl alkanol[7]. | [Synthesis]
Under nitrogen, a solution of 5-bromopyrimidine (1 g, 6.3 mmol) in 60 mL anhydrous THF was added BuLi (2.5 M, 2.6 mL, 6.5 mmol) at -78° C. The resulting yellow solution was stirred for 20 min, after which ethyl formate (0.55 mL, 6.7 mmol) was added dropwise over 5 min. After 20 min, the reaction was quenched with 1.5 M THF/HCl solution (4.5 mL, 6.7 mmol). The cold bath was removed, and the reaction mixture was stirred for 1 h. THF was removed in vacco, 10 mL of water was then added. The mixture was extracted with CHCl3 (2*10 mL), and the combined organics were dried (MgSO4) and concentrated. The crude product was purified via flash column chromatography (5 per cent MeOH/CHCl3) to give 0.35 g (51 per cent) of the titled Pyrimidine-5-carboxaldehyde.
| [References]
[1] Journal of medicinal chemistry, 2004, vol. 47, # 20, p. 4829 - 4837
[2] Patent: US2005/70712, 2005, A1. Location in patent: Page/Page column 42
[3] Patent: US2005/171131, 2005, A1. Location in patent: Page/Page column 41
[4] Patent: US9212138, 2015, B2. Location in patent: Page/Page column 42
[5] ChemMedChem, 2017, vol. 12, # 3, p. 257 - 270 |
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