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[ CAS No. 115-69-5 ] {[proInfo.proName]}

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Chemical Structure| 115-69-5
Chemical Structure| 115-69-5
Structure of 115-69-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 115-69-5 ]

CAS No. :115-69-5 MDL No. :MFCD00004678
Formula : C4H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :UXFQFBNBSPQBJW-UHFFFAOYSA-N
M.W : 105.14 Pubchem ID :1531
Synonyms :

Calculated chemistry of [ 115-69-5 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 26.41
TPSA : 66.48 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : -1.83
Log Po/w (WLOGP) : -1.31
Log Po/w (MLOGP) : -1.06
Log Po/w (SILICOS-IT) : -1.04
Consensus Log Po/w : -0.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.79
Solubility : 653.0 mg/ml ; 6.21 mol/l
Class : Highly soluble
Log S (Ali) : 0.95
Solubility : 941.0 mg/ml ; 8.95 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.45
Solubility : 299.0 mg/ml ; 2.84 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 115-69-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P304+P340+P312-P305+P351+P338-P337+P313 UN#:3259
Hazard Statements:H290-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 115-69-5 ]

* 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 [ 115-69-5 ]

[ 115-69-5 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 77-49-6 ]
  • [ 115-69-5 ]
YieldReaction ConditionsOperation in experiment
With methanol; nickel at 40 - 80℃; Hydrogenation;
With ethanol; nickel at 20℃; Hydrogenation;
With sulfuric acid; iron; iron(II) sulfate
With hydrogenchloride; tin
With ethanol; hydrogen bromide; sodium

  • 3
  • [ 115-69-5 ]
  • [ 105-58-8 ]
  • [ 6629-85-2 ]
YieldReaction ConditionsOperation in experiment
70% With sodium methylate In ethanol at 109.85℃; for 48h;
67% at 140℃; 5 4-(hydroxymethyl)-4-methyloxazolidin-2-one [0194] A flask with 2-amino-2-methyl-l,3-propanediol (3.32 g, 31.6 mmol) and diethyl carbonate (10 ml, 83 mmol) was fitted with a Dean-Stark trap and condenser and the suspension heated to 140 0C until 5 ml of liquid had been collected in the trap (~8 hr). The solution was cooled to RT slowly, and the resulting white, block crystals were filtered off (2.79 g, 21.3 mmol, 67%). The supernatant was purified by flash chromatography to afford the title compound as a white solid (1.04 g, 7.94 mmol, 25%). 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 3H), 2.2 (br s, 1 H), 3.56 (m, 2H), 4.06 (d, J=8.8 Hz, IH), 4.33 (d, J=8.8 Hz, IH), 5.2-5.3 (br s, IH). ESI/APCI calculated for C5H9NO3: 131.06. Found: 132 (MH+).
63% at 140℃; for 6h; Dean-Stark; 15.A Step A: 4-(Hydroxymethyl)-4-methyloxazolidin-2-one A solution of 2-amino-2-methylpropane-1,3-diol (3.32 g, 31.6 mmol) and diethyl carbonate (9.80 g, 83 mmol) was heated to 140 °C with a dean-stark trap for 6 hrs. The mixture was cooled down to rt and left at rt overnight. A white solid precipitated out. It was filtered and washed with small amount of cold methanol. The white solid was dried under vacuum to provide 4-(Hydroxymethyl)-4-methyloxazolidin-2-one (2.60 g, 19.8 mmol, 63% yield). LC/MS(M+1): 132.0; ‘H NMR (400MHz, CD3OD) ö ppm 4.34 (d, J=8.6 Hz, 1H), 4.02 (d, J=8.6 Hz, 1H), 3.52 - 3.37 (m, 2H), 1.28 (s, 3H).
  • 4
  • [ 50-00-0 ]
  • [ 115-69-5 ]
  • [ 71-43-2 ]
  • [ 7747-34-4 ]
  • 5
  • [ 2955-65-9 ]
  • [ 115-69-5 ]
  • [ 60204-80-0 ]
  • 6
  • [ 100-52-7 ]
  • [ 115-69-5 ]
  • [ 91340-32-8 ]
YieldReaction ConditionsOperation in experiment
(1) Benzaldehyde (17.4 ml) was added dropwise to a solution of 2-amino-2-methyl-1,3-propanediol (20 g) in methanol (200 ml) at 0 C. and the whole was stirred at room temperature for 2 hours. Sodium borohydride (11.5 g) was added thereto in portions at 0 C. and the mixture was stirred for 10 minutes. 1N Sodium hydroxide solution and ethyl acetate were added and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo to give 2-benzylamino-2-methyl-1,3-propanediol (28.54 g). NR (CDCl3, delta): 1.08 (3H, s), 3.54 (4H, s), 3.73 (2H, s), 7.20-7.45 (5H, m)
  • 9
  • [ 74685-00-0 ]
  • [ 115-69-5 ]
  • 2,4-dimethyl-4-hydroxymethyl-2-(tertiobutyldimethylsilyloxy)methyloxazolidine [ No CAS ]
  • 10
  • [ 1143-72-2 ]
  • [ 115-69-5 ]
  • [ 167566-29-2 ]
YieldReaction ConditionsOperation in experiment
60% With tetraethylammonium perchlorate In methanol at 25℃; electrolysis;
  • 11
  • [ 115-69-5 ]
  • [ 58479-61-1 ]
  • [ 280753-14-2 ]
  • 2-(<i>tert</i>-butyl-diphenyl-silanyloxy)-1-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-1-methyl-ethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 81% 2: 1.4% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;
  • 12
  • [ 14511-59-2 ]
  • [ 115-69-5 ]
  • C21H26ClN3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% In 1,4-dioxane Heating;
  • 13
  • [ 115-69-5 ]
  • [ 207557-35-5 ]
  • 1-[[[2-hydroxy-1-(hydroxymethyl)-1-methylethyl]amino]acetyl]-2-cyano-(S)-pyrrolidine [ No CAS ]
  • 14
  • [ 115-69-5 ]
  • [ 530-62-1 ]
  • [ 6629-85-2 ]
YieldReaction ConditionsOperation in experiment
99.7% In tetrahydrofuran at 0 - 20℃;
  • 15
  • anhydrons potassium carbonate [ No CAS ]
  • [ 1556-34-9 ]
  • [ 115-69-5 ]
  • 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; ethanol 13 EXAMPLE 13, 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydochoride EXAMPLE 13 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydochoride Bromination of 9-methylacridine (Lancaster Synthesis Ltd., P.O. Box 1000, Industrial Drive, Wyndham, NH 03087) by the procedure of A. Campbell et al , J . Chem . Soc . 1145 (1958) gave 9-bromomethylacridine. To a round bottomed flask equipped with magnetic stirring bar, condenser, and nitrogen inlet tube and bubbler was added 9-bromomethylacridine (10.5g, 38.58 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich Chemical Co., Milwaukee, WI, 53201, 4.06g, 38.58 mmol), anhydrons potassium carbonate (Mallinckrodt Co., St. Louis, MO, 53147, 10.50g, 76.0 mmol) and abs. ethanol (150 ML). The mixture was refluxed for 4 hours, cooled and filtered. The solvent was then removed by rotary evaporation. The crude product was dissolved in methanol (200 ML) filtered again and diluted to 2L with diethyl ether. The dark coloured crude product wasthen recrystallized one additional time from methanol+/diethyl ether and then twice from methanol to give 2-[(9-Acridinylmethyl)amino]-2-methyl-1,3-propanediol 0.6H2 mp 210-211°(d), which analyzed correctly for the assigned strucure (C,H,N,Cl).
  • 16
  • [ 69812-29-9 ]
  • [ 115-69-5 ]
  • 2-acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With triethylamine; In 1,4-dioxane; at 0 - 20℃; for 17h; a) To a stirred solution of 2-amino-2-methyl-1,3-propanediol (1.86 g, 17.7 mmol) in dioxane (20 ml) was added at 0 C. (ice water bath) commercially available <strong>[69812-29-9]2-acetamido-4-methylthiazole-5-sulfonyl chloride</strong> (1.5 g, 5.89 mmol) and triethylamine (0.9 ml, 6 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by flash chromatography on silica gel (ethyl acetate/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield 2-acetamido-4-methylthiazole-5-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (0.33 g, 17%) as a white solid. MS (ISP) 322.2 [(M-H)-]; mp 201 C.
  • 17
  • [ 89-01-0 ]
  • [ 6164-77-8 ]
  • [ 115-69-5 ]
  • N,N'-Bis(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With NMM; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; In aq CF3 COOH; ethanol; N,N-dimethyl-formamide; acetonitrile; EXAMPLE 7 N,N'-bis-(1,3-dihydroxy-2-methylprop-2-yl)pyrazine-2,3-dicarboxamide STR22 <strong>[89-01-0]Pyrazine-2,3-dicarboxylic acid</strong> (34 mg, 0.2 mmol), PyBOP (229 mg, 0.44 mmol), HOBt (60 mg, 0.44 mmol) and NMM (0.7 mL, 0.64 mmol) were dissolved in DMF (2 mL) and allowed to react for 10 min. 2-Amino-2-methyl-1,3-propanediol (46 mg, 0.44 mmol) was then added and stirring was continued overnight. The entire reaction mixture was then fractionated on a RP-HPLC column (Vydac 218TP1022, 22*250 mm, 10 mL/min, 0 to 15% MeCN in 0.1% aq CF3 COOH over 40 min). Appropriate fractions were pooled, rechromatographed and lyophilised to yield the pure title compound. Alternatively, the title compound was synthesised as follows: dimethylpyrazine-2,3-dicarboxylate (1.5 g, 7.7 mmol) and 2-amino-2-methyl-1,3-propanediol (1.6 g, 15.4 mmol) in absolute ethanol (5 mL) were heated under reflux during 4 hours. The reaction mixture was then cooled and the solvent was removed under reduced pressure. The residue was chromatographed on a flash silica gel column using CHCl3 /MeOH (4:1) as the eluant. Solvents were removed in vacuo and the pure title compound (2.2 g, 85%) was obtained after recrystallisation from isopropanol/hexane. 1 H-NMR (300 MHz, CDCl3): delta 1.06 (s, 6H, 2*Me), 3.48 (d, J=6.3 Hz, 8H, 4*CH2), 4.29 (t, J=6.3 Hz, 4H, 4*--OH), 7.64 (s, 2H, 2*NH), 8.38 (s, 2H, 2*CH). 13 C-NMR (75 MHz, CDCl3): delta 164.26 (CO), 145.54 (C-2,3), 143.59 (C-5,6), 65.30 (CH2), 58.66 (Cq), 18.13 (Me).
  • 18
  • [ 1556-34-9 ]
  • [ 60-29-7 ]
  • [ 115-69-5 ]
  • 2-[(9-Acridinylmethyl)amino]-2methyl-1,3-propanediol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.3% In methanol; ethanol 13 2-[(9-Acridinylmethyl)amino]-2methyl-1,3-propanediol dihydrochloride To a RB flask equipped with magnetic stirring bar, condenser, and N2 inlet line with bubbler was added 9-bromomethylacridine (10.5 g, 39.58 mmol), 2-amino-2-methyl-1,3-propanediol (Aldrich, 4.06 g, 38.58 mmol), anhydrous K2 CO3 (Mallinckrodt, 10.50 g, 76.0 mmol) and abs. EtOH (250 mL). The mixture was refluxed for 4 h, cooled and filtered. The solvent was then removed by rotary evaporation. The crude product was dissolved in CH3 OH (200 mL) filtered again and diluted to 2 L with Et2 O. The dark colored crude product was then recrystallized one additional time from CH3 OH/Et2 O and then twice from CH3 OH to give 3.46 g (24.3% yield) of 2-[(9-acridinylmethyl)amino]-2-methyl-1,3-propanediol dihydrochloride 0.6 H2 O, mp 210°-211° (dec), (C,H,N,Cl).
  • 19
  • [ 6629-85-2 ]
  • [ 112-16-3 ]
  • of4-hydroxymethyl-4-methyloxazolidin-2-one [ No CAS ]
  • [ 115-69-5 ]
  • [ 105-58-8 ]
  • 4-(dodecanoyloxymethyl)-4-methyloxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium ethanolate; triethylamine In dichloromethane; toluene 27 Preparation of 4-(dodecanoyloxymethyl)-4-methyloxazolidin-2-one EXAMPLE 27 Preparation of 4-(dodecanoyloxymethyl)-4-methyloxazolidin-2-one A solution of 10.5 g of 2-amino-2-methyl-1,3-propanediol and 12.3 g of diethyl carbonate, 0.5 g of sodium ethoxide in 100 ml of toluene was refluxed for 20 hours, cooled and concentrated at reduced pressure to give 13.6 g of crude product. Recrystallization from ethanol gave 9.23 g (67%) of4-hydroxymethyl-4-methyloxazolidin-2-one, m.p. 115 C. To a solution of 2.62 g of 4-hydroxymethyl-4-methyloxazolidin-2-one and 5 ml of triethylamine in 100 ml of dichloromethane was added dropwise 4.6 g of dodecanoyl chloride in 10 ml of dichloromethane. After 3 hours at room temperature the reaction mixture was concentrated, the residue was taken up in ether and washed with aqueous sodium bicarbonate. The ether layer was dried and concentrated to give 4.33 g (69%) of a thick yellow oil. Recrystallization from dichloromethane/hexane (1:10) gave 2.73 g (45%) of white crystals, m.p. 53-55 C.
  • 20
  • [ 115-69-5 ]
  • [ 58479-61-1 ]
  • [ 280753-14-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-Amino-2-methylpropane-1,3-diol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.916667h; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 0 - 20℃; for 17h; 9.1 Stage 1 : Preparation of 2-Amino-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propan-1-olSodium hydride (55% in dispersion in oil) (1.141 g) was added portion wise to a solution of 2-Amino-2-methyl-propane-1 ,3-diol (2.50 g) in dry THF (35 ml) at 00C. The reaction mixture was stirred at R.T. for 55'. terf-Butyldiphenylsilyl chloride (6.54 g) in dry THF (10 ml) were added dropwise at 00C and the reaction mixture was stirred for 17 hrs at R.T.The reaction mixture was quenched with water (18 ml) and then, extracted thrice with ethyl ether. The two layers were separated. The organic layer was washed once with water and then, dried over sodium sulphate, filetered and concentrated under reduced pressure to yield 8.94 g of 2-Amino-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propan-1- ol as a crude product (containing minor impurities) which was used in the next step without any further purification.1H NMR (CDCI3) δ ppm: 7.68-7.62 (4H, m); 7.47-7.37 (6H); 3.52 (2H, dd); 3.39 (2H, dd); 1.09 (9H, s); 1.02 (3H, s).
Stage #1: 2-Amino-2-methylpropane-1,3-diol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 0 - 20℃; for 17h; Inert atmosphere; 12a.1 Sodium hydride (55% in dispersion in oil) (1.141 g) was added portion wise to a solution of 2-amino-2-methyl-propane-1,3-diol (2.50 g) in dry THF (35 ml) at 00C. The reaction mixture was stirred at room temperature for 1h. terf-Butyldiphenylsilyl chloride (6.54 g) in dry THF (10 ml) was added dropwise at 00C and the reaction mixture was stirred for 17 hrs at room temperature. The reaction mixture was quenched with water (18 ml) and extracted thrice with ethyl ether The two layers were separated and the organic layer was washed once with water and then dried over sodium sulphate, filtered and concentrated under reduced pressure to yield 8.94 g of 2-amino-3-(tert-butyl-diphenyl- silanyloxy)-2-methyl-propan-1-ol as a crude product which was used as such in Stage 2 described below. 1H NMR (CDCI3) δ ppm 7 68-7 62 (4H, m); 7.47-7.37 (6H); 3.52 (2H, dd); 3.39 (2H, dd); 1.09 (9H, s); 1.02 (3H, s).
  • 21
  • [ 66-72-8 ]
  • [ 115-69-5 ]
  • [ 1259390-53-8 ]
YieldReaction ConditionsOperation in experiment
90% In ethanol at 20℃; for 12h; 2-[(3-Hydroxy-5-(hydroxymethyl)-2-methylpyri-din-4-yl)methylene]amino}-2-methylpropane-1,3-diol (10). A mixture of 0.53 g (3.0 mmol) of pyridoxal, 10 mL of anhydrous ethanol, and 0.33 g (3.0 mmol) of 2-amino-2-methylpropane-1,3-diol was stirred for 12 h at room temperature, then the solvent was removed. Next, 10 mL of absolute diethyl ether was added to the residue, and the precipitate was ltered off and dried. Yield 0.73 g (90%), mp >300°. IR spectrum, ν, cm-1: 1635 (=N). 1 NMR spectrum [(CD3)2SO], δ, ppm: 1.21 s (3, 3), 2.34 s (3H, CH3), 3.50 s (4, 2), 4.63 s (2, 2), 7.76 s (1H, NCAr), 8.82 s (1H, H). Mass spectrum (MALDI-TOF), m/z: 255 [M + ]+. Found, %: C 56.44; H 7.53; N 10.65. C12H18N2O4. Calculated, %: C 56.69; H 7.08; N 11.02.
74% In methanol; water at 20℃;
  • 22
  • [ 50-00-0 ]
  • [ 4966-90-9 ]
  • [ 115-69-5 ]
  • [ 1394246-44-6 ]
  • 23
  • [ 4966-90-9 ]
  • [ 115-69-5 ]
  • 4-hydroxy-6-methyl-3-nitropyridin-2(1H)-one 1,3-dihydroxy-2-methylpropan-2-amine [ No CAS ]
  • 24
  • [ 126-11-4 ]
  • [ 115-69-5 ]
YieldReaction ConditionsOperation in experiment
With 5%-palladium/activated carbon; hydrogen In methanol at 60℃; for 10h; Preparaton of NMP and NMPD [0020] TN was evaluated for its potential to produced NMP & NMPD: N02 NMPD Six experiments were run: NEPD / DTPA / H20 / Pd-C / 600 psig H2 / 80C NEPD / H20 / Pd-C / 600 psig H2 / 80 C NEPD / H20 / Pd-C / 600 psig H2 / 100 C TN / H20 / Pd-C / 600 psig H2 / 80 C TN / MeOH / Pd-C / 600 psig H2 / 80 C TN / MeOH / Pd-C / 600 psig H2 / 60 C
  • 25
  • [ 394-50-3 ]
  • [ 115-69-5 ]
  • 2-((E)-(1, 3-dihydroxy-2-methylpropan-2-ylimino) methyl)-6-fluorophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; In methanol; at 20 - 50℃; General procedure: Equimolar quantities (0.5mmol) of <strong>[394-50-3]3-fluoro-salicylaldehyde</strong>, followed by the addition of various amines were dissolved in methanol (10mL) in the presence of ionic liquid (1molpercent) 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide and KOH (1molpercent). The reaction mixture stirred at room temperature for an hour and refluxed for 4?6h at 50°C. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature, the solid product formed was filtered, washed three times with water and methanol (2:1) mixture and dried. The crude was further purified by column chromatography using hexane and ethyl acetate (9:2) mixture as eluent (Scheme 1).
  • 26
  • [ 115-69-5 ]
  • [ 6629-85-2 ]
YieldReaction ConditionsOperation in experiment
In ethanol 1 4-(Hydroxymethyl)-4-methyloxazolidin-2-one 4-(Hydroxymethyl)-4-methyloxazolidin-2-one A Dean-Stark trap was fitted to a flask containing 2-amino-2-methyl-1,3-propanediol (21.62 g, 205.6 mmol) suspended in diethyl carbonate (40 ml, 330 mmol). The suspension was heated to 150° C. for 6 h, during which time approximately 12 ml of ethanol was distilled. The solution was cooled to RT overnight, and the resulting crystals were filtered and washed with cold ethanol. The crude material (˜90% purity) was used without further purification (24.82 g, 189.0 mmol, 92%). 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 3H), 2.2 (br s, 1H), 3.57 (m, 2H), 4.06 (d, 1H, J=8.8 Hz), 4.33 (d, 1H, J=8.8 Hz), 5.2 (br s, 1H). LRMS (ESI/APCI): 132 [M+H]+.
  • 27
  • [ 115-69-5 ]
  • [ 823-62-1 ]
  • 2-((5-amino-6-chloro-1,2,4-triazin-3-yl)amino)-2-methylpropane-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
28.2% With sodium hydrogencarbonate In 1,4-dioxane at 120 - 125℃; for 20h; Inert atmosphere; 13.1 Step 1 : Preparation of 2-((5-amino-6-chloro-l,2,4-triazin-3-yl)amino)-2- methylpropane-l ,3-diol (Compound 48) 3,6-Dichloro-l,2,4-triazin-5-amine (2.00 g, 12.12 mmol) and 2-amino-2- methylpropane-l,3-diol (1.53 g, 14.55 mmol), Dioxane (30 mL) and sodium bicarbonate (2.04 g, 24.25 mmol) were added to a round bottom flask. Nitrogen gas was purged into the reaction mixture for 10-15 minutes and the reaction mass was heated under stirring at 120- 125 °C for 20 hours. After completion of the reaction, the reaction mass was cooled to room temperature and filtered to remove salts. The filtrate dioxane solution was concentrated under vacuum to obtain the crude, which was purified by column chromatography (using DCM/Methanol as eluent) to give 2-((5-amino-6-chloro-l,2,4-triazin-3-yl)amino)-2- methylpropane- 1 ,3-diol (Compound 48) (0.80 g, 28.20% yield).
  • 28
  • [ 4090-55-5 ]
  • [ 115-69-5 ]
  • 2-(5,5-dimethyl-2-oxo-2λ5-1,3,2-dioxaphosphinan-2-ylamino)-2-methyl-propane-1,3-diol [ No CAS ]
  • 29
  • [ 115-69-5 ]
  • [ 616-38-6 ]
  • [ 6629-85-2 ]
YieldReaction ConditionsOperation in experiment
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,4-dimethyl-1,2,4-triazolium iodide In acetonitrile at 20℃;
  • 30
  • [ 115-69-5 ]
  • [ 129-64-6 ]
  • C13H17NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% In toluene at 120℃; for 0.266667h; Inert atmosphere; 1.1 (1) Preparation of compound 1 Take 5-norbornene-2,3-dicarboxylic anhydride (5.00g, 30.46mmol) and 2-amino-2-methyl-1,3-propanediol (3.80g, 36.14mmol) into a 250ml dry reaction flask In the medium, nitrogen was introduced for 10 minutes, and then 150 ml of anhydrous toluene was added, refluxed at 120° C. for 16 hours and installed with a water trap. After the completion of the reaction was confirmed by thin-layer chromatography, the solvent was removed by rotary evaporation, and the product was separated by silica gel column chromatography to obtain 5.21 g of a white solid with a yield of 68%.
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