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[ CAS No. 6622-92-0 ]

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2D
Chemical Structure| 6622-92-0
Chemical Structure| 6622-92-0
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Product Details of [ 6622-92-0 ]

CAS No. :6622-92-0MDL No. :MFCD00006105
Formula : C6H8N2O Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :124.14Pubchem ID :135408640
Synonyms :

Computed Properties of [ 6622-92-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 6622-92-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6622-92-0 ]

  • Upstream synthesis route of [ 6622-92-0 ]
  • Downstream synthetic route of [ 6622-92-0 ]

[ 6622-92-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 6622-92-0 ]
  • [ 69696-35-1 ]
Reference: [1] Patent: WO2013/96151, 2013, A1,
[2] Patent: US2016/176882, 2016, A1,
[3] Patent: WO2017/221092, 2017, A1,
[4] Patent: WO2017/221100, 2017, A1,
  • 2
  • [ 6622-92-0 ]
  • [ 69696-35-1 ]
Reference: [1] Yakugaku Zasshi, 1937, vol. 57, p. 579,581; dtsch. Ref. S. 109, 111[2] Chem.Abstr., 1937, p. 6238
  • 3
  • [ 6622-92-0 ]
  • [ 4472-45-1 ]
YieldReaction ConditionsOperation in experiment
82% With trichlorophosphate In toluene for 3 h; Reflux POCl3 (0.460 g, 3.0 mmol) was added to the solution of compound 13 (1.0 mmol) in 15 mL of toluene and the mixture was stirred at reflux for 3 hours. Redundant POCl3 was removed under reduced pressure and ice water (10mL) was added. The solution was adjusted to the pH 9-10 with sodium carbonate and then extracted with methyl tert-butyl ether (MTBE). The organic phase was dried over sodium sulfate, and the solvent was removed under reduced pressure to afford compound 14. (Yield: 82percent) MS (ESI) (m /z) [M+H]+ 143.1.
71% With ammonia In sodium chloride; dichloromethane; trichlorophosphate Part 1
Preparation of 2,4-dimethyl-6-chloropyrimidine.
METHOD:
20 g (16.1*10-2 mol) of 2,4-dimethyl-6-hydroxypyrimidine in suspension in 150 ml of phosphorus oxychloride are introduced into a 250 ml three-necked flask fitted with a thermometer, a condenser and a magnetic stirrer.
The mixture is heated at 90° C. for one and a half hours.
The mixture is then cooled and then evaporated to dryness.
The residue which crystallises at ambient temperature is added, in small portions, to a binary mixture consisting of dichloromethane (200 ml) and 10percent ammonia (300 ml), previously cooled to -5° C. in an ice bath containing sodium chloride.
The mixture is stirred cold for half an hour and the organic phase is then decanted off, washed with water until neutral and then dried over sodium sulphate, filtered and evaporated.
The yellow liquid obtained is filtered through a glass frit filled with silica using the dichloromethane/methanol (99/1) eluent system; the pure fractions collected are evaporated.
16.4 g of a colourless liquid which has a persistent odour and which crystallises in a refrigerator are obtained.
Yield: 71percent.
Elementary analysis for C6 H7 ClN2; molecular weight=142.5.
The 1 H and 13 C NMR and mass spectra are in accordance with the expected structure.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1769 - 1775
[2] Tetrahedron Letters, 1999, vol. 40, # 42, p. 7477 - 7478
[3] Patent: US5438058, 1995, A,
[4] Patent: US6093718, 2000, A,
  • 4
  • [ 6622-92-0 ]
  • [ 4472-45-1 ]
Reference: [1] Heterocycles, 2006, vol. 68, # 9, p. 1973 - 1979
[2] Helvetica Chimica Acta, 2001, vol. 84, # 5, p. 1112 - 1118
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 22, p. 6439 - 6442
  • 5
  • [ 6622-92-0 ]
  • [ 10025-87-3 ]
  • [ 4472-45-1 ]
Reference: [1] Chemische Berichte, 1902, vol. 35, p. 1577
  • 6
  • [ 124-42-5 ]
  • [ 141-97-9 ]
  • [ 6622-92-0 ]
YieldReaction ConditionsOperation in experiment
36% With sodium ethanolate In ethanol for 20 h; Reflux 2,6-dimethylpyrimidin-4-ol. Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol (200 mL). And the mixture was refluxed for 20 hours. Water (10 mL) was added to the mixture. The resultant mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane /methanol = 15: 1) to give 2,6-dimethylpyrimidin-4-ol as a yellow solid (3.43 g, 36percent). LRMS (M + H+) m/z: calcd 124.06; found 124.
29% With potassium carbonate In water at 20℃; for 0.25 h; Microwave irradiation General procedure: The corresponding amidine hydrochloride (2.54 mmol) and powdered K2CO3 (5.76 mmol) were dissolved in water (5.0 mL) in a 20-mL vessel. The β-keto ester (2.31 mmol) was added and the resulting mixture was irradiated for 5–15 min (see Table 2). Upon the end of the reaction (TLC, hexanes/EtOAc, 5:1), the mixture was diluted with sat. aq NH4Cl (5.0 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined organic phases were dried (anhyd Na2SO4) and filtered. The filtrate was rotary evaporated and the obtained crude product was purified by column chromatography [silica gel, hexane/EtOAc mixtures or recrystallized (EtOH)].
Reference: [1] Patent: WO2013/75083, 2013, A1, . Location in patent: Paragraph 00374; 00375
[2] Synthesis (Germany), 2016, vol. 48, # 23, p. 4246 - 4252
[3] Patent: US2012/95031, 2012, A1, . Location in patent: Page/Page column 159-160
  • 7
  • [ 141-97-9 ]
  • [ 6622-92-0 ]
YieldReaction ConditionsOperation in experiment
36% With sodium ethanolate In ethanol for 20 h; Reflux Ethyl 3-oxobutanoate (10.0 g, 77 mmol) and acetimidamide hydrochloride (7.23 g, 77 mmol) were added to the solution of sodium ethanolate (10.5 g, 154 mmol) in ethanol(200 mE). And the mixture was refluxed for 20 hours. Water (10 mE) was added to the mixture. The resultant mixture wasconcentrated to give a residue. The residue was purified bycolunm chromatography (silica gel, dichloromethane/methanol=1 5:1) to give 2,6-dimethylpyrimidin-4-ol as a yellowsolid (3.43 g, 36percent). ERMS (M+H) mlz: calcd 124.06. found124.
Reference: [1] Patent: US9206128, 2015, B2, . Location in patent: Page/Page column 181; 82
  • 8
  • [ 141-97-9 ]
  • [ 143-37-3 ]
  • [ 6622-92-0 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 9, p. 1931 - 1936
[2] Journal of Chemical Research, Miniprint, 1988, # 1, p. 326 - 345
  • 9
  • [ 143-37-3 ]
  • [ 603-69-0 ]
  • [ 6622-92-0 ]
Reference: [1] Helvetica Chimica Acta, 1958, vol. 41, p. 1806,1812
  • 10
  • [ 6622-92-0 ]
  • [ 69696-37-3 ]
Reference: [1] Patent: WO2013/96151, 2013, A1,
[2] Patent: US2016/176882, 2016, A1,
[3] Patent: WO2017/221092, 2017, A1,
[4] Patent: WO2017/221100, 2017, A1,
  • 11
  • [ 6622-92-0 ]
  • [ 83410-37-1 ]
YieldReaction ConditionsOperation in experiment
65% With iodine; sodium hydroxide In water at 80℃; for 2 h; Step A:
2,6-Dimethylpyrimidin-4-ol (5.0 g, 40 mmol) was dissolved in aqueous NaOH solution (50 mL, 1 M, 50 mmol).
To the solution was added iodine (10.2 g, 40 mmol).
The mixture was gradually heated to 80° C. and stirred for 2 h.
After cooling the mixture to room temperature, acetic acid was added to adjust the pH ˜6.
A precipitate formed and was collected by filtration.
The solid was washed with water and dried to give 5-iodo-2,6-dimethylpyrimidin-4-ol (6.51 g, 65percent). MS m/z 251.2 [M+H]+.
Reference: [1] Patent: US9617268, 2017, B2, . Location in patent: Page/Page column 398
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 22, p. 4251 - 4260
[3] Tetrahedron, 2007, vol. 63, # 9, p. 1931 - 1936
[4] Patent: US5466692, 1995, A,
[5] Patent: US2012/95031, 2012, A1, . Location in patent: Page/Page column 160
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