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Chemical Structure| 3977-29-5
Chemical Structure| 3977-29-5
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Product Details of [ 3977-29-5 ]

CAS No. :3977-29-5 MDL No. :MFCD00006095
Formula : C5H7N3O Boiling Point : -
Linear Structure Formula :- InChI Key :KWXIPEYKZKIAKR-UHFFFAOYSA-N
M.W : 125.13 Pubchem ID :135402055
Synonyms :

Safety of [ 3977-29-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3977-29-5 ]

* 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.

  • Upstream synthesis route of [ 3977-29-5 ]
  • Downstream synthetic route of [ 3977-29-5 ]

[ 3977-29-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 3977-29-5 ]
  • [ 5600-21-5 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 43, p. 5921 - 5934
[2] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439
[4] Bioorganic Chemistry, 2018, vol. 78, p. 258 - 268
  • 2
  • [ 3977-29-5 ]
  • [ 5600-21-5 ]
YieldReaction ConditionsOperation in experiment
54% Reflux Amixture of 6 g of isocytosine IV and 35 mL of freshlydistilled phosphorus oxychloride was refluxed till themixture became homogeneous, then the excess of thechlorinating agent was removed in a vacuum. Forcooling, the residue was mixed with ice and treatedwith 25percent aqueous ammonia to 8. The formedsuspension was filtered, the precipitate was washedwith water, crystallized from 50percent ethanol, and dried toa constant mass. Yield 3.7 g (54percent), mp 188° (mp182–183° [7]), Rf 0.79 (D). Found, percent: 41.74;4.05; N 29.35. C5H6ClN3. Calculated, percent: 41.83;4.21; N 29.27.
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 1, p. 79 - 87[2] Zhurnal Obshchei Khimii, 2015, vol. 85, # 1, p. 79 - 87,9
  • 3
  • [ 3977-29-5 ]
  • [ 10025-87-3 ]
  • [ 5600-21-5 ]
Reference: [1] Chemische Berichte, 1899, vol. 32, p. 2934[2] Chemische Berichte, 1902, vol. 35, p. 1570
  • 4
  • [ 3977-29-5 ]
  • [ 5734-71-4 ]
Reference: [1] Journal of Organic Chemistry, 1947, vol. 12, p. 293
  • 5
  • [ 3977-29-5 ]
  • [ 1749-68-4 ]
YieldReaction ConditionsOperation in experiment
68% at 80 - 105℃; for 4 h; 2-amino-4-hydroxy-6-methylpyrimidine (5 g) was added to phosphorous oxychloride (50 ml) and heated to 80 ° C for 1 hour,Add a few drops of DMF, the reaction heated to 105 , 3 hours after the formation of orange solution. Reaction cooling, spin dry, add toluene and then once,The residue was taken up in ice-cooled saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is followed by water and saltWashed with water, dried and dried to give a yellow solid (3 g, yield: 68percent).
Reference: [1] Patent: CN106478519, 2017, A, . Location in patent: Paragraph 0057; 0058; 0059; 0060; 0061; 0062
  • 6
  • [ 3977-29-5 ]
  • [ 6314-12-1 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 23, p. 3923 - 3928
[2] Journal of the Chemical Society, 1947, p. 41,45
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 766,768
  • 7
  • [ 3977-29-5 ]
  • [ 4214-85-1 ]
YieldReaction ConditionsOperation in experiment
81% at 20℃; for 3 h; 2-Amino-6-methyl-5-nitropyrimidin-4(3H)-oneTo a mixture of 2-amino-6-methylpyrimidin-4(3H)-one (50 g, 0.4 mol) in 250 mL of H2SO4 at 0 0C was added 40 mL of HNO3 with an additional funnel. After being stirred at room temperature for 3 h, the reaction mixture was slowly poured into 3.6 L of diethyl ether and stirred for 15 min. Decant the ether solution and added 1.0 L of ethyl acetate to the solid and stirred for 1O h. The solid (54.8 g, 81percent yield) was filtered and used for next step without any further purification.
69% at 6 - 20℃; for 3 h; In a two-neck round-bottom flask containing precooled sulfuricacid (3 mL) was added 2-amino-4-hydroxy-6-methylpyrimidine(1) (100 mg, 0.8 mmol). An effective temperature control isrequired to the nitration occur properly. Nitric acid (0.2 mL,3.0 mmol) was added to the solution dropwise maintaining thetemperature below 6 C using an ice bath. The mixture waswarmed to room temperature and stirred for 3 h. The reaction mixturewas added in cold ethyl ether (10 mL), remaining the temperaturebelow 10 C. The precipitate was filtered and dissolved inboiling 1 mol/L NaOH solution. Acetic acid was added to the solutionfor precipitation of the product (pH among 6–8). The solid wasfiltered under vacuum, washed with water (2 1 mL) and dried invacuum for 8 h. The pyrimidinone 2 was obtained in 69percent yield(117 mg)
Reference: [1] Synthetic Communications, 2009, vol. 39, # 12, p. 2244 - 2249
[2] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 6, p. 1151 - 1153
[3] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[4] Patent: WO2006/122003, 2006, A2, . Location in patent: Page/Page column 32; 34
[5] Nucleosides and Nucleotides, 1999, vol. 18, # 3, p. 363 - 376
[6] Croatica Chemica Acta, 2008, vol. 81, # 1, p. 147 - 156
[7] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[8] Yakugaku Zasshi, 1953, vol. 73, p. 635,638[9] Chem.Abstr., 1954, p. 9363
[10] Nippon Kagaku Zasshi, 1952, vol. 73, p. 862[11] Chem.Abstr., 1954, p. 2070
  • 8
  • [ 141-97-9 ]
  • [ 113-00-8 ]
  • [ 3977-29-5 ]
YieldReaction ConditionsOperation in experiment
52% at 20℃; for 10 h; The above compound was prepared using a previously reportedmethod with minor modifications [26] as shown in Scheme 1. To asolution of guanidine (2.02 g, 33.84 mM) in acetone/ethanol mixture(1:2), a solution of acetoacetic ester (4.40 g, 33.86 mM) in acetone/ethanol was added dropwise and the resulting solution wasstirred at room temperature for 10 h. The solid product obtainedwas separated by filtration and recrystallized from acetic acid toobtain colorless crystals.Yield: 1.36 g (52percent). 1H NMR (400 MHz, CDCl3, ppm), d: 11.09 (s,1H, OH), 5.92 (s, 2H, NH2), 5.14 (s, 1H, Ar–H), 2.14 (s, 3H, Ar–CH3).13C NMR (100 MHz, CDCl3, ppm) d: 162.3, 161.1, 155.3, 102.5, 23.9.ESI-MS calc. for C5H7N3O [M+]: 125.06; found 126.07 [M++1].
Reference: [1] Polyhedron, 2017, vol. 129, p. 141 - 148
  • 9
  • [ 3510-99-4 ]
  • [ 50-01-1 ]
  • [ 3977-29-5 ]
YieldReaction ConditionsOperation in experiment
62.1% at 100℃; for 3 h; Added to the mixture obtained in step a)Amount of anhydrous methanol dissolved,Into guanidine hydrochloride 95.5g (1mol)Heated to 100 reflux 3h,The mixture of solvents evaporated to dryness,Add the right amount of distilled water to just dissolve,Let cool to room temperature,With 1mol / L dilute hydrochloric acid to adjust the PH value to 6.5,A solid precipitation, suction filtration,Rinse with deionized water,The resulting wet finished product is at a temperature of 60 ° CVacuum drying oven available 12h availableAbout 77.7 g of 2-amino-4-hydroxy-6-methylpyrimidine.The product is 2-amino-4-hydroxy-6-methylpyrimidine,Purity of 99percentYield 62.1percent
Reference: [1] Patent: CN107188856, 2017, A, . Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0034-0039
  • 10
  • [ 50-01-1 ]
  • [ 141-97-9 ]
  • [ 3977-29-5 ]
Reference: [1] Bioorganic Chemistry, 2018, vol. 78, p. 258 - 268
  • 11
  • [ 50-01-1 ]
  • [ 105-45-3 ]
  • [ 3977-29-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2429 - 2439
  • 12
  • [ 593-85-1 ]
  • [ 141-97-9 ]
  • [ 3977-29-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2004, vol. 41, # 3, p. 343 - 348
  • 13
  • [ 3977-29-5 ]
  • [ 65996-58-9 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 24, p. 7947 - 7952
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 2, p. 226 - 231
[4] Patent: WO2006/122003, 2006, A2,
  • 14
  • [ 3977-29-5 ]
  • [ 63200-54-4 ]
Reference: [1] Patent: WO2006/122003, 2006, A2,
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