* 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.
Reference:
[1] Journal of Medicinal Chemistry, 1999, vol. 42, # 4, p. 669 - 676
4
[ 931-63-5 ]
[ 109-94-4 ]
[ 164738-44-7 ]
Reference:
[1] Journal of Organic Chemistry, 1995, vol. 60, # 12, p. 3781 - 3786
5
[ 931-63-5 ]
[ 75-36-5 ]
[ 1056174-56-1 ]
Yield
Reaction Conditions
Operation in experiment
97%
With cetyltrimethylammonim bromide; cetyltrimethylammonium chloride In 1,2-dichloro-ethane at 70℃; for 0.0833333 h; Microwave irradiation; Micellar solution
General procedure: The mixture of anisole(1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was treated with CTAB/CTAC, (0.001 mol), in dichloroethane and the resulting reaction mixture was heated in a controlled microwave synthesizer (BiotageInitiator+SP Wave model (0.200W at 2.45 GHz, capped at 60W duringsteady state) for 5 min (attains temperature 100 C and 2 bar pressure). The final product (3o) was isolated by absorbing the reaction mixture into silica geland purifying it by column chromatography using ethyl acetate–petroleumether as the eluent.
Geschw. d. Isomerisierung unter versch. Bed. --> 1.2-Dihydro-1-methyl-2-oxo-pyrimidin: Br., Fo., l.c.S. 4912;
Photolyse in Me. u. i. Ggw. v. N(C2H5)3 u. HN(C2H5)2;
Kinetik d. n-Butylaminolyse: S.2323;
Yield
Reaction Conditions
Operation in experiment
2-Chlorpyrimidin, Me., Na-Methylat-Lsg. <Δ>;
Pyrimid-2-yl-trimethylammoniumchlorid, NaOCH3;
1, Photolyse;
5-Brom-2-methoxy-pyrimidin, Photolyse;
Pyrimidin-2-SO2F (R=H, X=F), NaOCH3;
2-Chlor-pyrimidin, KOMe, N2H4, Pd/CaCO3;
6 Synthesis of Compound 6
To 2-methoxypyrimidine obtained were added 14 ml of trifluoroacetic acid, 3 ml of trifluoroacetic anhydride and 3.96 g (16.94 mmol) of N-iodosuccinimide, and the mixture was stirred under reflux (bath temperature: 80° C.) for 11 hours.
23
[ 931-63-5 ]
benzhydroximic acid chloride[ No CAS ]
5-methoxy-3-phenyl-8aH-[1,2,4]oxadiazolo[4,5-c]pyrimidine[ No CAS ]
2-methoxy-5-[(Z)-(hydroxyimino)(phenyl)methyl]pyrimidine[ No CAS ]
8-bromomethyl-4-hydroxy-6-[3-(2-methoxy-pyrimidin-5-yl)-acryloyl]-2-methyl-3,6,7,8-tetrahydro-3,6-diaza-<i>as</i>-indacene-1-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 6 steps
1: TFA, trifluoroacetic anhydride, N-iodosuccinimide / 11 h / 80 °C
2: 88 percent / Pd(OAc)2, K2CO3, n-Bu4NCl / dimethylformamide / 1 h / 80 °C
3: 96 percent / 4N aq. KOH / methanol / 2 h / 50 °C
4: 90 percent / Et3N, 2-chloro-1-methylpyridinium chloride / CH2Cl2 / 2 h / 50 °C
5: 1.) NaH / 1.) DMF, -20 deg C, 260 min, 2.) DMF, 80 min
6: 48 percent aq. HBr / acetonitrile / 0.5 h / Ambient temperature
methyl (1S)-1-(bromomethyl)-7-methyl-5-<(4-methylpiperazinyl)carbonyloxy>-3-<2-(4-methoxy-3,5-pyrimidinyl)ethen-1-ylcarbonyl>-1,2-dihydro-3H-pyrrolo<3,2-e>indole-8-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 8 steps
1: TFA, trifluoroacetic anhydride, N-iodosuccinimide / 11 h / 80 °C
2: 88 percent / Pd(OAc)2, K2CO3, n-Bu4NCl / dimethylformamide / 1 h / 80 °C
3: 96 percent / 4N aq. KOH / methanol / 2 h / 50 °C
4: 90 percent / Et3N, 2-chloro-1-methylpyridinium chloride / CH2Cl2 / 2 h / 50 °C
5: 1.) NaH / 1.) DMF, -20 deg C, 260 min, 2.) DMF, 80 min
6: 48 percent aq. HBr / acetonitrile / 0.5 h / Ambient temperature
7: Et3N / CH2Cl2; toluene / 0.5 h / -78 °C
8: CH2Cl2; toluene / 0.33 h / -78 - 0 °C
8-bromomethyl-6-[3-(2-methoxy-pyrimidin-5-yl)-acryloyl]-2-methyl-4-(4-nitro-phenoxycarbonyloxy)-3,6,7,8-tetrahydro-3,6-diaza-<i>as</i>-indacene-1-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 7 steps
1: TFA, trifluoroacetic anhydride, N-iodosuccinimide / 11 h / 80 °C
2: 88 percent / Pd(OAc)2, K2CO3, n-Bu4NCl / dimethylformamide / 1 h / 80 °C
3: 96 percent / 4N aq. KOH / methanol / 2 h / 50 °C
4: 90 percent / Et3N, 2-chloro-1-methylpyridinium chloride / CH2Cl2 / 2 h / 50 °C
5: 1.) NaH / 1.) DMF, -20 deg C, 260 min, 2.) DMF, 80 min
6: 48 percent aq. HBr / acetonitrile / 0.5 h / Ambient temperature
7: Et3N / CH2Cl2; toluene / 0.5 h / -78 °C
With cetyltrimethylammonim bromide; cetyltrimethylammonium chloride In 1,2-dichloro-ethane at 70℃; for 0.0833333h; Microwave irradiation; Micellar solution;
General procedure for microwave-assisted synthesis
General procedure: The mixture of anisole(1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was treated with CTAB/CTAC, (0.001 mol), in dichloroethane and the resulting reaction mixture was heated in a controlled microwave synthesizer (BiotageInitiator+SP Wave model (0.200W at 2.45 GHz, capped at 60W duringsteady state) for 5 min (attains temperature 100 C and 2 bar pressure). The final product (3o) was isolated by absorbing the reaction mixture into silica geland purifying it by column chromatography using ethyl acetate-petroleumether as the eluent.
A solution of <strong>[17180-94-8]5-chloropyrimidine</strong> (5 mmol) and MeONa (5.5 mmol) in THF (30 mL) was stirred overnight at 150 C. After cooling to rt, the solvent was removed and water (20 mL) was added to the residue. The resulting mixture was extracted with EtOAc (3 x 35 mL). The combined organic layers were washed with brine, and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound.
2-methoxypyrimidine (28 g, 0.26 mol) was dissolved in tetrahydrofuran (200 ml) at -60 C.The prepared TMP.MgCl.LiCl solution was added dropwise, and after the addition was completed, the mixture was stirred for 1 hour.Anhydrous zinc chloride (39 g, 0.28 mol) was added, and the temperature was slowly raised to room temperature, and bromine (45 g, 0.28 mol) was added dropwise, after 2 hours.The reaction was quenched by adding 1 mol/L aqueous hydrochloric acid to pH 7.The aqueous layer was separated and extracted with ethyl acetate (200 ml * 3 times), and the organic layer was combined and dried.Purification by column chromatography (PE: EA = 10:1) gave 8.3 g (yield: 17%). Preparation TMP.MgCl.LiCl: Magnesium (8 g, 0.33 mol) and anhydrous lithium chloride (15 g, 0.33 mol) were placed in a dry three-necked flask, and a solution of 2-chloropropane (28.5 g, 0.3 mol) in tetrahydrofuran (200 ml) was added.After the addition was completed, stir at room temperature for 2 hours.Add 2,2,6,6-tetramethylpiperidine (60 g. 0.36 mol), stir overnight, to obtain a brown solution TMP.MgCl.LiCl;