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Chemical Structure| 89380-14-3 Chemical Structure| 89380-14-3

Structure of 89380-14-3

Chemical Structure| 89380-14-3

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Product Details of [ 89380-14-3 ]

CAS No. :89380-14-3
Formula : C6H6Cl2N2O
M.W : 193.03
SMILES Code : COCC1=CN=C(Cl)N=C1Cl
English Name :2,4-Dichloro-5-(methoxymethyl)pyrimidine
MDL No. :MFCD18837147
InChI Key :DZTIREGQZKBGID-UHFFFAOYSA-N
Pubchem ID :21813641

Safety of [ 89380-14-3 ]

Application In Synthesis of [ 89380-14-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 89380-14-3 ]

[ 89380-14-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ CAS Unavailable ]
  • [ 89380-14-3 ]
  • [ 1796592-94-3 ]
YieldReaction ConditionsOperation in experiment
39% With triethylamine In tetrahydrofuran; acetonitrile at 0 - 20℃; 18 To a 0 °C solution of 2,4-dichloro-pyrimidine 3 (0.17 g, 0.88 mmol) in CH3CN (15 mL) was added benzylamine (0.22 g, 2.0 mmol). The reaction wasstirred overnight at room temperature. The resulting mixture was concentrated under vacuum, and the residue was purified by flash chromatography using a mixture of hexane and ethyl acetate to afford N-benzyl-2-chloro-5- (methoxymethyl)pimidin-4-amine 4 (0.09 g, 39%). LRMS (M + H+) mlz:calcd 264.08; found 264.
  • 2
  • [ 1887069-93-3 ]
  • [ 89380-14-3 ]
  • [ 1887069-26-2 ]
YieldReaction ConditionsOperation in experiment
35.5% Stage #1: (R)-3-hydroxy-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino-[5',6':4,5]thieno[3,2-f]quinolin-8-one With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 2,4-dichloro-5-(methoxymethyl)pyrimidine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; 96 Synthesis of (R)-3-((2-chloro-5-(methoxymethyl)pyrimidin-4-yl)oxy)-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one (I-96) To a stirred suspension of INT-6 (203.3 mg, 0.68 mmol) in anhydrous DMF (17 mL) was added t-BuOK (1 M in THF, 1.36 mL, 1.36 mmol) at 0° C. dropwise to give a brown solution. The resulting solution was stirred for further 0.5 h at this temperature. INT-63 (262.2 mg, 1.36 mmol) in DMF (3 mL) was added dropwise to the above solution and stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate (40 mL) and water (50 mL), the organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×40 mL). The combined organic layers were washed with brine (80 mL) and the organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by preparative HPLC afforded I-96 (110.4 mg, 35.5%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.37 (d, J=9.2 Hz, 1H), 8.72 (s, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.14 (d, J=4.4 Hz, 1H), 7.87 (d, J=8.8 Hz, 1H), 7.64 (d, J=9.2 Hz, 1H), 7.18-7.16 (m, 1H), 4.62 (s, 2H), 3.62-3.61 (m, 1H), 3.51-3.47 (m, 2H), 3.42 (s, 3H), 1.19 (d, J=6.8 Hz, 3H). MS m/z (M+H): 455.9.
  • 3
  • [ CAS Unavailable ]
  • [ 7627-38-5 ]
  • [ 89380-14-3 ]
YieldReaction ConditionsOperation in experiment
59% In methanol for 5h; Cooling with ice; 31.2 Step 2 The compound 55 (2.42 g, 12.3 mmol) was dissolved in methanol (24.2 mL). Under ice cooling, NaOMe (28% MeOH solution, 2.37 g, 12.26 mmol) was slowly added to the solution. The mixture was stirred for 5 hours. Under ice cooling, 10% citric acid was added to the reaction mixture to render the reaction mixture acidic. The mixture was extracted with ethyl acetate. The organic layer was washed by brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica-gel column chromatography (ethyl acetate-n-hexane) to give the compound 56 (1.41 g, yield 59%).
  • 4
  • [ 89380-14-3 ]
  • [ 2032242-00-3 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydroxide In tetrahydrofuran; water for 8h; 31.3 Step 3 The compound 56 (1.41 g, 7.30 mmol) was dissolved in tetrahydrofuran (14.1 mL). A 2 mol/L aqueous solution of sodium hydroxide (7.30 mL, 14.6 mmol) was added to the solution. The mixture was stirred for 8 hours. Under ice cooling, a 2 mol/L aqueous solution of hydrochloric acid was added to the reaction mixture to render the reaction mixture acidic. NaCl was added to the mixture until saturated. The mixture was extracted with chloroform. The organic layer was washed by brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The obtained solids were washed by a solvent of ethyl acetate:n-hexane = 1:1 to give the compound 57 (0.75 g, yield 58%).
  • 5
  • [ 124461-06-9 ]
  • [ 89380-14-3 ]
YieldReaction ConditionsOperation in experiment
32.26% With trichlorophosphate In methanol at 25 - 120℃; 35.2 Step 2. Preparation of 2,4-dichloro-5-(methoxymethyl)pyrimidine A suspension of 5-(methoxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (0.5 g, 1 eq, 3.2 mmol) in phosphoroyl trichloride (5 mL) at 25 °C was heated to 120 °C and stirred at 120 °C for 12 hours. LCMS showed the starting material peak was consumed and the desired peak was detected. The reaction mixture was concentrated under reduced pressure to give a residue.The residue was purified by prep-TLC (eluted with petroleum ether/ethyl acetate = 2/1, Rf = 0.4) to afford 0.2 g (32.26%) of 2,4-dichloro-5-(methoxymethyl)pyrimidine as a yellow solid. LCMS (ESI+): Rt = 0.639 min, m/z 193.1 (M+H)+
32.26% With trichlorophosphate In methanol at 25 - 120℃; 35.2 Step 2. Preparation of 2,4-dichloro-5-(methoxymethyl)pyrimidine A suspension of 5-(methoxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (0.5 g, 1 eq, 3.2 mmol) in phosphoroyl trichloride (5 mL) at 25 °C was heated to 120 °C and stirred at 120 °C for 12 hours. LCMS showed the starting material peak was consumed and the desired peak was detected. The reaction mixture was concentrated under reduced pressure to give a residue.The residue was purified by prep-TLC (eluted with petroleum ether/ethyl acetate = 2/1, Rf = 0.4) to afford 0.2 g (32.26%) of 2,4-dichloro-5-(methoxymethyl)pyrimidine as a yellow solid. LCMS (ESI+): Rt = 0.639 min, m/z 193.1 (M+H)+
 

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