[ CAS No. 582313-57-3 ]

Name: 4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine
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Quality Control of [ 582313-57-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 582313-57-3 ]

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Alternatived Products of [ 582313-57-3 ]

Product Details of [ 582313-57-3 ]

CAS No. :	582313-57-3	MDL No. :	MFCD12924542
Formula :	C₆H₃ClFN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	171.56	Pubchem ID :	11321224
Synonyms :

Computed Properties of [ 582313-57-3 ]

TPSA :Topological Polar Surface Area	41.6	H-Bond Acceptor Count :	3
XLogP3 :	1.7	H-Bond Donor Count :	1
SP3 :	0.00	Rotatable Bond Count :	0

Safety of [ 582313-57-3 ]

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

Application In Synthesis of [ 582313-57-3 ]

Upstream synthesis route of [ 582313-57-3 ]
Downstream synthetic route of [ 582313-57-3 ]

[ 582313-57-3 ] Synthesis Path-Upstream 1~3

1
[ 22276-95-5 ]
[ 582313-57-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -78℃; for 0.25 h;	[4-CHLORO-5-BROMO-7H-PYRROLO] [2,3-d] pyrimidine 2 (0.6 g, 2.60 [MMOL)] was dissolved in 30 mL THF (dry), then [COOLED TO-78°C] before adding 4.10 mL nBuLi (1.6 [M] in hexane) dropwise over a period of 10 minutes. The mixture was stirred for 20 minutes [AT-78°C] before adding 3.38 mmol N- fluorobenzene sulfonimide (NFSI) (1.065 g in 6.5 mL dry THF) dropwise over a period of 15 minutes. The mixture was warmed to room temperature overnight, quenched with 2 mL water, and then evaporated to dryness. The crude preparation obtained was partitioned between ethyl acetate (EtOAc) and a saturated solution of ammonium chloride (40 mL/20 mL) then the aqueous layer was extracted with 20 mL of EtOAc and the combined organic layers were washed with 20 mL water. The organic layer was dried with [MGS04,] filtered, and the solvent was evaporated. The crude was purified on silica-gel (silica-gel solid deposit in [MEOH)] with 4percent MeOH/CH2CI2 to provide the title compound (0.36 g, [71 percent YIELD)] ; [1H] NMR (DMSO) : [8] 7.70 (s, 1H) ; 8.62 (s, [1H)] ; 12.25 (s, NH)

Reference： [1] Patent: WO2004/11478, 2004, A2, . Location in patent: Page 27
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5284 - 5297
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7742 - 7747
[4] Patent: WO2015/143712, 2015, A1, . Location in patent: Page/Page column 34; 35
[5] Patent: US2016/244475, 2016, A1, . Location in patent: Paragraph 0310; 0313

2
[ 3680-69-1 ]
[ 582313-57-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With Selectfluor In acetic acid; acetonitrile at 20 - 70℃; for 14 h;	4-CHLORO-7H-PYRROLOPYRIMIDINE 1 (5 g, 32.7 mmol) and Selectfluor (17.35 g, 49 mmol) were placed in a round bottom flask, followed by the addition of dry acetonitrile (250 mL) and ACOH (50 mL). The solution was then heated at 70 °C for 14 h under N2. After cooling to room temperature, the solvent was removed in vacuo and co-evaporated with toluene (50 mL x 2). The solid was dissolved in a mixture of DCM : EtOAc (1: 1) and filtered through a pad of silica gel which was thoroughly washed. The combined washings were evaporated. And the crude product was then subjected to column chromatography with DCM: EtOAc (4: 1) to give 3.3 g (59percent yield) of 2 as a white SOLID. 1H NMR (DMSO-d6) 8 7.73 (s, 1H), 8.64 (s, 1H), 12.5 (br s, 1H); 13C NMR (DMSO-d6) 8 105.3 (d, J= 14.3 Hz), 111.0 (d, J= 25. 5 Hz), 139.6 (d, J= 244.5 Hz), 146.7 (d, J= 1.5 Hz), 148. 5 (d, J= 3.8 Hz), 151.0 ; 19F NMR (DMSO-D6) 8-170. 7 ( d, J= 1.6 Hz): Mass spectroscopy (MS) measured for C6H3C1FN3 (M+H): 172.0, observed: 172.0.
58%	With acetic acid; Selectfluor In acetonitrile at 70℃; for 18 h; Inert atmosphere	To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (2.00 g) in acetonitrile (100 mL) were added acetic acid (20 mL) and N-fluoro-N'-(chloromethyl)triethylenediamine bis(tetrafluoroborate) (6.92 g), and the mixture was stirred under nitrogen atmosphere at 70°C for 18 hours. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added methylene chloride/ethyl acetate (1/1), and the solution was passed through a column packed with silica gel (100 mL) and then extracted with methylene chloride/ethyl acetate = 1/1 (2 L). The extract was concentrated, and the resulting residue was purified by column chromatography on silica gel (hexane/ethyl acetate = 70/30 to 35/65) to give 4-chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine (1.30 g) as a powder (yield: 58percent). MS(APCI)m/z; 172/174[M+H]⁺.
41%	With acetic acid; Selectfluor In acetonitrile at 70℃;	PREPARATION 144-chloro-5-fluoro-1 /-/-pyrrolo[2,3-c ]pyrimidineA mixture of 6-chloro-7-deazapurine (0.5 g, 3.26 mmol) and Selectfluor^.(R). (1.730 g, 4.88 mmol) in CH₃CN (25 mL) was treated with AcOH (5 mL) and heated at 70 °C overnight before being cooled and concentrated. Toluene was added and the mixture was concentrated. The residue was dissolved in 1 :1 EtOAc/CH₂CI₂ and filtered through a pad of silica gel. The filtrate was concentrated and purified via flash column chromatography (20percent EtOAc/CH₂CI₂) to afford the title compound (0.226 g, 41 percent) as a pink solid. ¹H NMR (400 MHz, DMSO-d₆) δ ppm 12.50 (br. s, 1 H), 8.60 - 8.66 (m, 1 H), 7.73 (t, J = 2.51 Hz, 1 H); MS (m/z) 171.9 (M+H⁺).

26%

With acetic acid; Selectfluor In acetonitrile at 70℃; for 16 h;

The solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimi- dine Q-1 (10 g, 65.1 mmol) and Selectfluor (27.7 g, 78.1 mmol) in CH3CN (500 mE) and AcOH (100 mE) was stirred at 70° C. for 16 h. (The reaction was done four times, 10 g of Q-1 in each vessel). The reaction solution turned from colorless to black. TEC (CH2C12/CH3OH=20: 1) showed 20percent of the starting material remained, and then the reaction solution was concentrated to give crude solid. The solid was dissolved in EtOAc (1 E), washed with H20 (300 mEx2). The organic layer was concentrated to give Q-2 (7 g) as brown solid. The combined batch four batches were purified by prep-HPEC (0.225percent formic acid/acetonitrile) to give Q-2 (11.6 g, 26percent) as a white solid. ECMS [M+1] 172; ‘H NMR (400 MHz, DMSO-d5) ö ppm 12.47 (s, 1H), 8.62 (s, 1H), 7.72 (d, 1H)

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2004, vol. 23, # 1-2, p. 161 - 170
[2] Patent: WO2005/16878, 2005, A2, . Location in patent: Page/Page column 12
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7297 - 7298
[4] Patent: EP2390254, 2011, A1, . Location in patent: Page/Page column 54
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 2052 - 2062
[6] Journal of the American Chemical Society, 2008, vol. 130, # 41, p. 13639 - 13648
[7] Patent: WO2011/149827, 2011, A1, . Location in patent: Page/Page column 67
[8] Patent: US2016/244475, 2016, A1, . Location in patent: Paragraph 0310; 0311
[9] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4518 - 4522
[10] Antimicrobial Agents and Chemotherapy, 2010, vol. 54, # 7, p. 2932 - 2939
[11] Patent: WO2011/146882, 2011, A1, . Location in patent: Page/Page column 111
[12] Patent: US2012/122838, 2012, A1, . Location in patent: Page/Page column 81
[13] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7742 - 7747
[14] Patent: WO2015/143712, 2015, A1,
[15] Patent: US2016/244475, 2016, A1,

3
[ 582313-56-2 ]
[ 582313-57-3 ]

Reference： [1] Patent: WO2006/65335, 2006, A2, . Location in patent: Page/Page column 21; 22

[ 582313-57-3 ] Synthesis Path-Downstream 1~1

1
[ 6974-32-9 ]
[ 582313-57-3 ]
[ 750598-19-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 - 80℃; for 1.41667h;	N, O-BIS (TRIMETHYLSILYL) ACETAMIDE (BSA, 0.16 mL, 0.64 mmol) was added to a stirred suspension of 4-chloro-5-fluoro-7H-pyrrolo [2, 3-d] pyrimidine (0.1 g, 0. 58 mmol) in dry acetonitrile (4 mL). After stirring at room temperature for 10 min, 1-O-ACETYL-2, 3, 5,-TRI-0- BENZOYL-P-D-RIBOFURANOSE (0.322 g, 0.64 mmol) was added, followed by the addition of trimethylsily trifluoromethanesulfonate (0.115 mL, 0.64 mmol). The reaction was stirred at room temperature for 15 min after which it was transferred to a preheated oil bath at 80°C. After stirring for 1 hour at 80°C, the reaction was cooled to room temperature and diluted with EtOAc (25 mL). The organic phase was then sequentially washed with saturated. NAHCO3 and brine, dried (MGS04) and concentrated to provide the crude nucleoside. Purification by column chromatography (SI02, 10-25percent EtOAc in hexanes) provided protected nucleoside (6) as a white foam (232 mg, 65percent). 1H NMR (CDC13) B : 8.63 (s, 1H), 8. 11 (d, 2H, J= 7.1 Hz), 8.01 (d, 2H, J= 7.1 Hz), 7.91 (d, 2H, J= 7.1 Hz), 7. 65-7. 33 (M, 9H), 7.17 (d, 1H, J= 2.6 Hz), 6.69 (dd, 1H J= 6.2, 1.1 Hz), 6.09 (M, 2H), 4.87 (dd, 1H, J= 12. 1,3. 0 Hz), 4.78 (dd, 1H, J= 7.2, 3.7 Hz), 4.67 (dd, 1H, J = 12. 1,3. 7 Hz). 13C NMR (CDC13) 8 : 166.1, 165.4, 165.1, 151.9, 151.1, 147.1, 143.7- 140. 3 (C-F-coupling), 133. 8, 133. 7, 133. 6,129. 8,129. 8,129. 7,129. 3,128. 7,128. 7, 128. 6, 128.5, 128.4, 109.5-109. 1 (C-C-F-coupling), 108.3-108. 1 (C-C-F-coupling), 86. 3,80. 6,73. 9, 71.4, 63.6. MS (M+H): 616.1, observed: 616.1.

Reference： [1]Nucleosides, nucleotides and nucleic acids,2004,vol. 23,p. 161 - 170
[2]Patent: WO2005/16878,2005,A2 .Location in patent: Page/Page column 12-13
[3]Journal of the American Chemical Society,2008,vol. 130,p. 13639 - 13648

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H221	Flammable gas
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H261	In contact with water releases flammable gas
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H316	Causes mild skin irritation
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H330	Fatal if inhaled
H331	Toxic if inhaled
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H336	May cause drowsiness or dizziness
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 582313-57-3 ]

Quality Control of [ 582313-57-3 ]

Related Doc. of [ 582313-57-3 ]

Product Details of [ 582313-57-3 ]

Computed Properties of [ 582313-57-3 ]

Safety of [ 582313-57-3 ]

Application In Synthesis of [ 582313-57-3 ]

[ 582313-57-3 ] Synthesis Path-Upstream 1~3

[ 582313-57-3 ] Synthesis Path-Downstream 1~1

Related Functional Groups of [ 582313-57-3 ]

Fluorinated Building Blocks

Chlorides

Related Parent Nucleus of [ 582313-57-3 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 582313-57-3 ]

Related Parent Nucleus of
[ 582313-57-3 ]