ChemicalBook CAS DataBase List Methyl 2,4-dichloropyrimidine-6-carboxylate

Methyl 2,4-dichloropyrimidine-6-carboxylate synthesis

6synthesis methods

Product Name:Methyl 2,4-dichloropyrimidine-6-carboxylate
CAS Number:6299-85-0
Molecular formula:C6H4Cl2N2O2
Molecular Weight:207.01

To a stirred suspension of orotic acid (20.00 g, 128.140 mmol) in POCI3(75 ml) was added DMF (catalytic amount, -0.5 ml) at ambient temperature, and the resulting reaction mixture was refluxed for 3 h. Excess of POC was removed by vacuum distillation after 3h of reflux. The obtained slurry was poured slowly into a 5 per cent mixture of methanol in chloroform (200 ml) at 0°C and stirred for 30 min. The organic layer obtained was washed with a saturated solution of NaHCC>3 (3 x 200 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure, yielding Methyl 2,4-dichloropyrimidine-6-carboxylate (19.00 g, 91 .800 mmol).

67-56-1 Synthesis

67-56-1
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$9.00/25ml

65-86-1 Synthesis

65-86-1
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$5.00/100mg

Methyl 2,4-dichloropyrimidine-6-carboxylate

6299-85-0
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$10.00/1g

Yield:6299-85-0 19 g

Reaction Conditions:

Stage #1: orotic acidwith trichlorophosphate in N,N-dimethyl-formamide; for 3 h;Reflux;
Stage #2: methanol in chloroform;N,N-dimethyl-formamide at 0;

Steps:

1.a Step a

To a stirred suspension of orotic acid (CAS Number 65-86-1 , available from Alfa Aesar) (20.00 g, 128.140 mmol) in POCI₃(75 ml) was added DMF (catalytic amount, -0.5 ml) at ambient temperature and the resulting reaction mixture was refluxed for 3 h. Excess of POC was removed by vacuum distillation after 3h of reflux. The obtained slurry was poured slowly in 5% mixture of methanol in chloroform (200 ml) at 0°C and stirred for 30 min. The organic layer obtained was washed with saturated solution of NaHCC>3 (3 x 200 ml). The combined organic phase was dried over Na2S0₄, filtered and concentrated under reduced pressure yielding methyl 2,6-dichloropyrimidine-4-carboxylate (19.00 g, 91 .800 mmol), which was used in the next step without further purification.

References:

WO2018/167276,2018,A1 Location in patent:Paragraph 00131; 00132; 00133

6153-44-2 Synthesis