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[ CAS No. 102-52-3 ]

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2D
Chemical Structure| 102-52-3
Chemical Structure| 102-52-3
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Product Details of [ 102-52-3 ]

CAS No. :102-52-3MDL No. :MFCD00008488
Formula : C7H16O4 Boiling Point : 183°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :164.20Pubchem ID :66019
Synonyms :

Computed Properties of [ 102-52-3 ]

TPSA : 36.9 H-Bond Acceptor Count : 4
XLogP3 : 0.3 H-Bond Donor Count : 0
SP3 : 1.00 Rotatable Bond Count : 6

Safety of [ 102-52-3 ]

Signal Word:DangerClass:3
Precautionary Statements:P210-P403+P235UN#:1993
Hazard Statements:H225Packing Group:
GHS Pictogram:

Application In Synthesis of [ 102-52-3 ]

  • Upstream synthesis route of [ 102-52-3 ]
  • Downstream synthetic route of [ 102-52-3 ]

[ 102-52-3 ] Synthesis Path-Upstream   1~30

  • 1
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YieldReaction ConditionsOperation in experiment
23% With potassium carbonate In ethanol; water EXAMPLE 4
2(1 H)-Pyrimidinethione, 1-methyl
To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion.
The resulting mixture was stirred at 25° C. for 18 h, then spin-evaporated in vacuo.
The residue was dissolved in H2O (1.25 L).
The solution was made alkaline by the portionwise addition of K2CO3 and extracted with CH2Cl2 (4*500 mL).
The combined extracts were dried over MgSO4 and spin-evaporated in vacuo to a solid.
The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23percent) of product; mp 186-188° C. (uncorrected).
An additional reaction was performed to give a total of 40.7 g.
23% With potassium carbonate In ethanol; water EXAMPLE 4
2(1H)-Pyrimidinethione, 1-methyl
To a stirred mixture of 1-methyl-2-thiourea (76.6 g, 0.85 mol) and malonaldehyde bis(dimethyl acetal) (126.8 g, 0.77 mol) in EtOH (1.5 L) was added 10 M HCI (76.6 mL, 0.77 mol) in one portion.
The resulting mixture was stirred at 25° C. for 18 h, then spin-evaporated in vacuo.
The residue was dissolved in H2O (1.25 L).
The solution was made alkaline by the portionwise addition of K2CO3 and extracted with CH2Cl2 (4*500 mL).
The combined extracts were dried over MgSO4 and spin-evaporated in vacuo to a solid.
The crude product was recrystallized from EtOH (600 mL) then dried to constant weight in vacuo at room temperature to give 22.9 g (23percent) of product; mp 186-188° C. (uncorrected).
An additional reaction was performed to give a total of 40.7 g.
Reference: [1] Patent: US2002/12639, 2002, A1,
[2] Patent: US6495125, 2002, B2,
  • 2
  • [ 102-52-3 ]
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YieldReaction ConditionsOperation in experiment
179.4mg for 2 h; Reflux a)
1-(2-Methoxyphenyl)-1H-pyrazol
200 mg of 2-methoxyphenyl hydrazine hydrochloride was dissolved in 5 ml of ethanol, and 189 μl of malonaldehyde bisdimethylacetal was added and heated at reflux for 2 hours.
To the reaction mixture was added 50 ml of water, neutralized with a saturated aqueous solution of sodium carbonate, and extracted with 60 ml of ethyl acetate.
After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to yield 179.4 mg of the title compound.
1H-NMR (CDCl3); δ (ppm) 3.87 (3H, s), 6.42 (1H, d, J=2.4 Hz), 7.02-7.07 (2H, m), 7.27-7.32 (1H, m), 7.68-7.72 (2H, m), 8.01 (1H, d, J=2.4 Hz).
MS (FAB); m/z 175 (M+H)+
179.4 mg for 2 h; Reflux 200 mg of 2-methoxyphenylhydrazine hydrochloride was dissolved in 5 ml of ethanol and 189 μl of malonaldehyde bisdimethylacetal was added, followed by heating to reflux for 2 hours. To the reaction mixture was added 50 ml of water, followed by neutralizing with a saturated aqueous sodium carbonate solution and extracting with 60 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and subsequently the solvent was distilled off under reduced pressure to afford 179.4 mg of the title compound. 1H-NMR (CDCl3); δ (ppm) 3.87 (3H, s), 6.42 (1H, d, J=2.4 Hz), 7.02-7.07 (2H, m), 7.27-7.32 (1H, m), 7.68-7.72 (2H, m), 8.01 (1H, d, J=2.4 Hz). MS (FAB); m/z 175 (M+H)+
179.4 mg for 2 h; Reflux a) 1-(2-Methoxyphenyl)-1H-pyrazole [0154] 200 mg of 2-methoxyphenylhydrazine hydrochloride was dissolved in 5 ml of ethanol and 189 µl of malonaldehyde bisdimethylacetal was added, followed by heating to reflux for 2 hours. To the reaction mixture was added 50 ml of water, followed by neutralizing with a saturated aqueous sodium carbonate solution and extracting with 60 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and subsequently the solvent was distilled off under reduced pressure to afford 179.4 mg of the title compound. 1H-NMR(CDCl3); δ (ppm) 3.87 (3H,s), 6.42 (1H, d, J=2.4Hz), 7.02-7.07 (2H, m), 7.27-7.32 (1H, m), 7.68-7.72 (2H, m), 8.01 (1H, d, J=2.4Hz). MS (FAB); m/z 175 (M+H)+
Reference: [1] Patent: US2013/317074, 2013, A1, . Location in patent: Paragraph 0333; 0334; 0335
[2] Patent: US2014/30209, 2014, A1, . Location in patent: Paragraph 0146; 0147; 0148
[3] Patent: EP2881114, 2015, A1, . Location in patent: Paragraph 0154
  • 3
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  • [ 102908-37-2 ]
YieldReaction ConditionsOperation in experiment
179.4 mg for 2 h; Reflux 200 mg of 2-methoxyphenylhydrazine hydrochloride was dissolved in 5 ml of ethanol and 189 μl of malonaldehyde bisdimethylacetal was added, followed by heating to reflux for 2 hours. To the reaction mixture was added 50 ml of water, followed by neutralizing with a saturated aqueous sodium carbonate solution and extracting with 60 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and subsequently the solvent was distilled off under reduced pressure to afford 179.4 mg of the title compound. 1H-NMR (CDCl3); δ (ppm) 3.87 (3H,s), 6.42 (1H, d, J=2.4Hz), 7.02-7.07 (2H, m), 7.27-7.32 (1H, m), 7.68-7.72 (2H, m), 8.01 (1H, d, J=2.4Hz). MS (FAB); m/z 175 (M+H)+
179.4 mg for 2 h; Reflux [0176] 200 mg of 2-methoxyphenylhydrazine hydrochloride was dissolved in 5 ml of ethanol and 189 μl of malonaldehyde bisdimethylacetal was added, followed by heating to reflux for 2 hours. To the reaction mixture was added 50 ml of water, followed by neutralizing with a saturated aqueous sodium carbonate solution and extracting with 60 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and subsequently the solvent was distilled off under reduced pressure to afford 179.4 mg of the title compound. [0177] 1H-NMR (CDCl3); δ (ppm) 3.87 (3H, s), 6.42 (1H, d, J=2.4 Hz), 7.02-7.07 (2H, m), 7.27-7.32 (1H, m), 7.68-7.72 (2H, m), 8.01 (1H, d, J=2.4 Hz). [0178] MS (FAB); m/z 175 (M+H)+
Reference: [1] Patent: EP2889031, 2015, A1, . Location in patent: Paragraph 0128
[2] Patent: US2015/209301, 2015, A1, . Location in patent: Paragraph 0176-0178
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Reference: [1] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 6
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Reference: [1] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 5-6
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Reference: [1] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 6
  • 7
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Reference: [1] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 5
  • 8
  • [ 107-25-5 ]
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Reference: [1] Patent: DE821201, 1949, ,
[2] DRP/DRBP Org.Chem.,
[3] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 57,58,61;engl.Ausg.S.65,67,68
[4] Patent: US6395914, 2002, B1, . Location in patent: Page column 4
[5] Patent: US6395914, 2002, B1, . Location in patent: Page column 5
[6] DRP/DRBP Org.Chem.,
[7] Patent: US2527533, 1946, ,
  • 9
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  • [ 98561-07-0 ]
Reference: [1] Patent: US6355844, 2002, B1, . Location in patent: Example 8
[2] Patent: US6395914, 2002, B1, . Location in patent: Page column 5-6
  • 10
  • [ 107-25-5 ]
  • [ 149-73-5 ]
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  • [ 55546-58-2 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 13, p. 2920 - 2925
  • 11
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  • [ 107-02-8 ]
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  • [ 14315-97-0 ]
  • [ 2806-84-0 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 42, p. 9846 - 9854
  • 12
  • [ 67-56-1 ]
  • [ 107-02-8 ]
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  • [ 14315-97-0 ]
  • [ 2806-84-0 ]
  • [ 19060-10-7 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 42, p. 9846 - 9854
  • 13
  • [ 67-56-1 ]
  • [ 4190-06-1 ]
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Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 12, p. 4135 - 4139
  • 14
  • [ 926-65-8 ]
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  • [ 102-52-3 ]
Reference: [1] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 5
[2] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 5
[3] Patent: EP1607381, 2005, A1, . Location in patent: Page/Page column 5
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Reference: [1] Patent: US6355844, 2002, B1, . Location in patent: Example 1
[2] Patent: US6355844, 2002, B1, . Location in patent: Example 9
[3] Patent: US6355844, 2002, B1, . Location in patent: Example 5
[4] Patent: US6355844, 2002, B1, . Location in patent: Example 2
  • 16
  • [ 108-05-4 ]
  • [ 149-73-5 ]
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Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1987, vol. 23, # 3, p. 316 - 320[2] Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 3, p. 376 - 381
[3] Patent: US2459076, 1948, ,
[4] Patent: US2459076, 1948, ,
  • 17
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  • [ 98561-07-0 ]
  • [ 102-52-3 ]
Reference: [1] Patent: US2823226, 1954, ,
[2] Patent: US2823226, 1954, ,
  • 18
  • [ 67-56-1 ]
  • [ 1165952-92-0 ]
  • [ 7424-91-1 ]
  • [ 102-52-3 ]
  • [ 108-59-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1990, # 2, p. 185 - 188
[2] Liebigs Annalen der Chemie, 1990, # 2, p. 185 - 188
[3] Liebigs Annalen der Chemie, 1990, # 2, p. 185 - 188
  • 19
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Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6024 - 6027
[2] Journal of Organic Chemistry, 1990, vol. 55, # 24, p. 6024 - 6027
  • 20
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  • [ 19060-10-7 ]
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Reference: [1] , 1970, vol. 6, p. 421 - 426[2] Zhurnal Organicheskoi Khimii, 1970, vol. 6, p. 422 - 428
  • 21
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  • [ 107-02-8 ]
Reference: [1] Human and Experimental Toxicology, 1999, vol. 18, # 11, p. 677 - 682
  • 22
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Reference: [1] Human and Experimental Toxicology, 1999, vol. 18, # 11, p. 677 - 682
  • 23
  • [ 67-56-1 ]
  • [ 624-67-9 ]
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Reference: [1] Pharmaceutical Chemistry Journal, 1973, vol. 7, # 9, p. 545 - 549[2] Khimiko-Farmatsevticheskii Zhurnal, 1973, vol. 7, # 9, p. 6 - 11
  • 24
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Reference: [1] Bulletin de la Societe Chimique de France, 1968, p. 1129 - 1135
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Reference: [1] Monatshefte fuer Chemie, 1990, vol. 121, p. 203 - 207
[2] Monatshefte fuer Chemie, 1990, vol. 121, p. 203 - 207
  • 26
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  • [ 7705-08-0 ]
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Reference: [1] Patent: US2459076, 1948, ,
[2] Patent: US2459076, 1948, ,
  • 27
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  • [ 149-73-5 ]
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Reference: [1] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 57,58,61;engl.Ausg.S.65,67,68
  • 28
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  • [ 31230-17-8 ]
  • [ 116834-96-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 17, p. 2706 - 2725
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  • [ 6825-71-4 ]
  • [ 1260169-02-5 ]
YieldReaction ConditionsOperation in experiment
58.1% at 100℃; for 14 h; To a solution of ethyl 3,5-diamino-lH-pyrazole-4-carboxylate (5.00 g, 29.38 mmol) in DMF (80 mL) were added 1 , 1 ,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol) and AcOH (0.34 mL, 5.88 mmol). The reaction mixture was stirred at 100 °C for 14 h, and then concentrated in vacuo. The residue was partitioned between DCM (50 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with DCM (100 mL x 3). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (a solution of NH3in MeOH (7 M)/DCM (v/v) =1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1percent).MS (ESI, pos. ion) m/z: 207.1 [M+H]+; H NMR (400 MHz, CDC1 ): δ (ppm) 8.60 (dd, J= 4.40 Hz, 1.76 Hz, 1H), 8.46 (dd, J = 6.76 Hz, 1.76 Hz, 1H), 6.86 (dd, J = 6.72 Hz, 4.40 Hz, 1H), 4.50 (q, J = 7.08 Hz, 2H), 1.47 (t, J = 7.08 Hz, 3H).
58.1% With acetic acid In N,N-dimethyl-formamide at 100℃; for 14 h; To a solution of ethyl 3,5-diamino-1 -hydro-pyrazole-4-carboxylate (5.00 g, 29.38 mmol)In N, N-dimethylformamide ((80 mL)1,1,3,3-tetramethoxypropane (14.50 mL, 88.15 mmol)And acetic acid (0.34 mL, 5.88 mmol).After the reaction mixture was stirred at 100 ° C for 14 hours,Concentrate under reduced pressure. The resulting residue was dispersed in a mixed system of dichloromethane (50 mL) and water (50 mL), the organic phase was separated and the aqueous phase was extracted with dichloromethane (100 mL x 3). The combined organic phases were washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH3 in methanol (7M) / methylene chloride (v / v) = 1/100) to give the title compound as a pale yellow solid (3.52 g, 58.1percent).
35.3% With triethylamine In N,N-dimethyl-formamide at 100℃; for 14 h; ethyl 2-aminopyrazolo[l ,5-a]pyrimidine-3-carboxylateA mixture of ethyl 3,5-diamino-l H-pyrazole-4-carboxylate (1.0 g, 5.9 mmol), 1,1,3,3- tetramethoxypropane (2.9 mL, 18 mmol), triethylamine (2 mL, 10 mmol), and DMF (15 mL) was heated at 100 0C for 14 hrs, then a further 2 mL of 1,1,3,3-tetramethoxypropane was added. After adding the additional 1,1,3,3-tetramethoxypropane, a significant by-product was noted and heating was stopped immediately. The reaction was cooled to room temperature and the DMF was removed in vacuo. The residue was partitioned between DCM and water, then the organic layer was concentrated and the residue purified by silica chromatography, eluting with 95:5 DCM: 2M methanolic ammonia solution to afford 420 mg (35percent) of ethyl 2-aminopyrazolo[l,5- a]pyrimidine-3-carboxylate. 1H NMR (500 MHz, CDCl3) δ 8.57 (dd, J = 4.3, 1.6, IH), 8.43 (dd, J = 6.7, 1.6, IH), 6.84 (dd, J = 6.7, 4.4, IH), 5.52 (s, 2H), 4.48 (q, J= 7.1, 2H), 1.45 (t, J= 7.1, 3H).
Reference: [1] Patent: WO2015/73267, 2015, A1, . Location in patent: Paragraph 318
[2] Patent: CN104650092, 2017, B, . Location in patent: Paragraph 0463-0464; 0473-0474
[3] Patent: WO2011/3065, 2011, A2, . Location in patent: Page/Page column 110-111
[4] Patent: US2015/336962, 2015, A1, . Location in patent: Paragraph 0478
[5] Patent: WO2017/48702, 2017, A1, . Location in patent: Paragraph 001169; 001170; 001172
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Reference: [1] Patent: WO2011/63233, 2011, A1, . Location in patent: Page/Page column 32
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