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[ CAS No. 1060816-67-2 ]

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2D
Chemical Structure| 1060816-67-2
Chemical Structure| 1060816-67-2
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Product Details of [ 1060816-67-2 ]

CAS No. :1060816-67-2MDL No. :MFCD13189420
Formula : C7H6ClN3 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :167.60Pubchem ID :57415888
Synonyms :

Computed Properties of [ 1060816-67-2 ]

TPSA : 30.7 H-Bond Acceptor Count : 2
XLogP3 : 1.6 H-Bond Donor Count : 0
SP3 : 0.14 Rotatable Bond Count : 0

Safety of [ 1060816-67-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1060816-67-2 ]

  • Upstream synthesis route of [ 1060816-67-2 ]
  • Downstream synthetic route of [ 1060816-67-2 ]

[ 1060816-67-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 335654-06-3 ]
  • [ 74-88-4 ]
  • [ 1060816-67-2 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sodium hydride In acetonitrile at 5 - 20℃; for 0.5 h;
Stage #2: at 0 - 20℃;
Step-1: 2-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [0182] To a stirred solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (1 g, 6.5 mmol) in MeCN (25 mL) at 5 oC was added NaH (313 mg, 7.8 mmol). The resultant mixture was brought to room temperature and stirred for 30 min. Then MeI was added at 0 oC and continued stirring at room temperature for overnight. The reaction mixture was filtered through a pad of celite and washed with MeCN (10 mL). The filtrate was concentrated and recrystallized from Et2O. The mother liquor was concentrated and purified by ISCO (SiO2: DCM/EtOAc 0 to 30percent). Altogether, the recrystallized and purified provided the pure compound (835 mg, 77percent).
47% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; Sealed tube Step 1. 2-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineTo a solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (27 mg, 0.16 mmol, prepared as reported in Bioorganic and Medicinal Chemistry Letters, 16(22), 5778-5783 (2006)) in DMF (0.15 mL) was added potassium carbonate (67 mg, 0.48 mmol), followed by methyl iodide (10 microL, 0.16 mmol). The mixture was stirred in a sealed vial at RT for 3 h. The reaction was diluted with DCM and acetonitrile, filtered and concentrated. The product was purified by flash column chromatography on silica gel, eluting with 0-50percent ethyl acetate in hexanes to afford product as a white solid (13 mg, 47percent). LCMS (M+H)+: 167.9, 169.9.
47.4%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: at 0 - 15℃; for 3 h;
To a solution of NaH (106.6 mg, 2.67 mmol) in THF (5 mL) was added 2-chloro- 7H-pyrrolo[2,3-d]pyrimidine (500 mg, 2.54 mmol) at 0°C and stirred for 30 minutes at the same temperature. CH3I (1.5 g, 10.2 mmol) was added at 0°C and the combined mixture stirred for 3 h at 15°C. After TLC showed the reaction was complete, the mixture was diluted with water 20 mL) and extracted with ethyl acetate EA (2x20 mL) and the combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the title compound (254 mg, 47.4percent) as colorless oil which was used in next step without further purification.
Reference: [1] Patent: WO2016/171755, 2016, A1, . Location in patent: Paragraph 0182
[2] Patent: US2010/298334, 2010, A1, . Location in patent: Page/Page column 44
[3] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00378
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