6-Chloro-4-pyrimidinecarboxylic acid
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6-Chloro-4-pyrimidinecarboxylic acid
structure -
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CAS No:
37131-91-2
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Formula:
C5H3ClN2O2
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Chemical Name:
6-Chloro-4-pyrimidinecarboxylic acid
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Synonyms:
4-Pyrimidinecarboxylic acid,6-chloro-;6-Chloro-4-pyrimidinecarboxylic acid
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CAS No:
6-Chloro-4-pyrimidinecarboxylic acid Basic Attributes
158.54
158.54
1312995-182-4
DTXSID20586250
2933599090
6-Chloro-4-pyrimidinecarboxylic acid Use and Manufacturing
30 mL of EtOAc was added to 2 g of 6-hydroxypyrimidine-4-carboxylic acid 1 and oxalyl chloride (3.75 mL, 3 eq, 0.043 mol) was added slowly to the mixture followed by a few drops of DMF (evolution of gas was observed). The reaction mixture was heated at 75To the solution of /e/V-butyl (oxiran-2-ylmethyl)carbamate (1 g, 5.77 mmol) in 10 mL of isopropanol, was added l, 2, 3, 4-tetrahydroisoquinoline (770 mg, 5.77 mmol). The solution was heated to reflux for 6 h and the volatile was removed under reduced pressure. The resulting residue was treated for 1 h with 5 mL of trifluoroacetic acid in 5 mL of (0811) dichloromethane. The solution was evaporated into dryness under reduced pressure. The resulting brown oil was used for next step without purification. The residue was added to the solution of To a solution of (21 mg, 0.130 mmol) was added to a stirring suspension of Compound 92 (100 mg, 0.157 mmol) and diisopropylethylamine (0.113 mL, 0.650 mmol) in acetonitrile (3 mL). The mixture was heated overnight at 80C. Several drops of water were added to the crude reaction mixture, and the resulting solution was purified by reverse phase chromatography using acetonitrile with 0.25% formic acid in water with 0.25% formic acid as the eluent. The impure product was triturated with hot acetonitrile to afford Compound 101 (18 mg, 15%) as a brown solid. LCMS (method A): m/z 723.6 (M+H)+. 'H NMR (CD3OD) delta 8.54 (s, 1H), 7.53 (d, 2H), 7.30 (d, 2H), 7.11 (s, H), 5.57 (br s, 1H), 4.52-4.32 (m, 3H), 3.71 (t, 2H), 3.59 (br s, 1H), 3.51-3.38 (m, 5H), 2.91-2.80 (m, 4H), 2.20-2.13 (m, 3H) 2.05-1.96 (m, 3H), 1.79-1.71 (m, 2H), 1.65-1.49 (m, 3H), 1.30-1.21 (m, 2H), 1.18-1.08 (m, 2H).To a solution of Compound 92 (48 mg, 0.07 mmol) and 6-chloropyrimidine-4- carboxylic acid (34 mg, 0.21 mmol) in DMSO (1 mL) was added DIEA (31 mu, 0.18 mmol). The solution mixture was heated in a microwave at 120C for one hour. The reaction was purified directly by MS-HPLC to afford Compound 14A (10 mg, 19%). LCMS (method A): m/z 741.3 (M+H)+. 'H NMR (DMSO) delta 9.20 (d, 1H), 9.12 (t, 1H), 8.23 (s, 1H), 7.96-7.82 (m, 2H), 7.68 (d, 2H), 7.35 (d, 2H), 5.67 (br s, 1H), 4.40-4.10 (m, 3H), 3.52 (br, 1H), 3.40-3.20 (m, 7H), 2.82-2.74 (m, 4H), 2.03 (t, 3H), 1.92-1.78 (m, 3H), 1.67 (d, 2H), 1.54-1.41 (m, 3H), 1.19-1.10 (m, 2H), 1.03-0.89 (m, 2H).
Computed Properties
Molecular Weight:158.54
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:157.9883050
Monoisotopic Mass:157.9883050
Topological Polar Surface Area:63.1
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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6-Chloro-4-pyrimidinecarboxylic acid
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