Home Cart Sign in  
Chemical Structure| 66224-66-6 Chemical Structure| 66224-66-6

Structure of 66224-66-6

Chemical Structure| 66224-66-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 66224-66-6 ]

CAS No. :66224-66-6
Formula : C5H5N5
M.W : 135.13
SMILES Code : N=C1N=CNC2=C1NC=N2

Safety of [ 66224-66-6 ]

Application In Synthesis of [ 66224-66-6 ]

* 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 [ 66224-66-6 ]
  • Downstream synthetic route of [ 66224-66-6 ]

[ 66224-66-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 105-36-2 ]
  • [ 66224-66-6 ]
  • [ 25477-96-7 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1 h; Inert atmosphere
Stage #2: for 2 h; Inert atmosphere
General procedure: To a suspension of 9H-purine (1c, 1.20 g, 10.0 mmol) in anhydrous DMF (15 mL) at 0 °C was added sodium hydride (0.48 g, 12.0 mmol) in batches and then stirred vigorously 1 hour at room temperature under argon. Ethyl bromoacetate (1.33 mL, 12.0 mmol) was added dropwise via syringe and stirred continuously for another 2 hours. The solvent was evaporated in vacuo pressure. Water (15 mL) was added to the residue and extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over Na2SO4, and evaporated, in vacuo. The residue was purified by chromatography on a silica gel column (30 × 6 cm). Elution with 1:2 to 1:3 hexanes- ethyl acetate gave 3a as white powder.
20% With potassium carbonate In water; N,N-dimethyl-formamide EXAMPLE 26
Synthesis of 9-carboxymethyladenine ethyl ester
Adenine (10 g, 74 mmol) and potassium carbonate (10.29 g, 74 mmol) were suspended in DMF and ethyl bromoacetate (8.24 mL, 74 mmol) was added.
The suspension was stirred for 2.5 h under nitrogen at room temperature and then filtered.
The solid residue was washed three times with DMF (10 mL).
The combined filtrate was evaporated to dryness, in vacuo.
Water (200 mL) was added to the yellowish-orange solid material and the pH adjusted to 6 with 4 N HCl.
After stirring at 0° C. for 10 minutes, the solid was filtered off, washed with water, and recrystallized from 96percent ethanol (150 mL).
The title compound was isolated by filtration and washed thoroughly with ether. Yield: 3.4 g (20percent). M.p. 215.5-220° C. Anal. for C9H11N5O2 found(calc.): C: 48.86(48.65); H: 5.01(4.91); N: 31.66(31.42).
1H-NMR (250 MHz; DMSO-d6): 7.25 (bs, 2H, NH), 5.06 (s, 2H, NCH2), 4.17 (q, 2H, J=7.11 Hz, OCH2) and 1.21 (t, 3H, J=7.13 Hz, NCH2).
13C-NMR. 152.70, 141.30, 61.41, 43.97 and 14.07. FAB-MS. 222 (MH+). IR: Frequency in cm-1 (intensity).
3855 (54.3), 3274(10.4), 3246(14.0), 3117(5.3), 2989(22.3), 2940(33.9), 2876(43.4), 2753(49.0), 2346(56.1), 2106(57.1), 1899(55.7), 1762(14.2), 1742(14.2), 1742(1.0), 1671(1.8), 1644(10.9), 1606(0.6), 1582(7.1), 1522(43.8), 1477(7.2), 1445(35.8) and 1422(8.6).
20% With potassium carbonate In water; N,N-dimethyl-formamide EXAMPLE 26
Synthesis of 9-carboxymethyladenine ethyl ester
Adenine (10 g, 74 mmol) and potassium carbonate (10.29 g, 74 mmol) were suspended in DMF and ethyl bromoacetate (8.24 mL, 74 mmol) was added.
The suspension was stirred for 2.5 h under nitrogen at room temperature and then filtered.
The solid residue was washed three times with DMF (10 mL).
The combined filtrate was evaporated to dryness, in vacuo.
Water (200 mL) was added to the yellowish-orange solid material and the pH adjusted to 6 with 4N HCl.
After stirring at 0° C. for 10 minutes, the solid was filtered off, washed with water, and recrystallized from 96percent ethanol (150 mL).
The title compound was isolated by filtration and washed thoroughly with ether. Yield: 3.4 g (20percent). M.p. 215.5°-220° C. Anal. for C9 H11 N5 O2 found(calc.): C: 48.86(48.65); H: 5.01(4.91); N: 31.66(31.42).
1 H-NMR (250 MHz; DMSO-d6): 7.25 (bs, 2H, NH2), 5.06 (s, 2H, NCH2), 4.17 (q, 2H, J=7.11 Hz, OCH2) and 1.21 (t, 3H, J=7.13 Hz, NCH2).
13 C-NMR. 152.70, 141.30, 61.41, 43.97 and 14.07. FAB-MS. 222 (MH+). IR: Frequency in cm-1: 3855, 3274, 3246, 3117, 2989, 2940, 2876, 2753, 2346, 2106, 1899, 1762, 1742, 1742, 1671, 1644, 1606, 1582, 1522, 1477, 1445 and 1422.
References: [1] Journal of Organic Chemistry, 1994, vol. 59, # 19, p. 5767 - 5773.
[2] Tetrahedron, 2005, vol. 61, # 34, p. 8295 - 8305.
[3] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 1, p. 19 - 26.
[4] Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 12, p. 1541 - 1545.
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2300 - 2313.
[6] Dalton Transactions, 2012, vol. 41, # 33, p. 10043 - 10051.
[7] Journal of the Chemical Society, Chemical Communications, 1993, # 9, p. 800 - 801.
[8] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 112 - 114[9] Bioorganicheskaya Khimiya, 1995, vol. 21, # 2, p. 130 - 132.
[10] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 7, p. 464 - 469[11] Bioorganicheskaya Khimiya, 1995, vol. 21, # 7, p. 539 - 544.
[12] Patent: US6414112, 2002, B1, .
[13] Patent: US6441130, 2002, B1, .
[14] Patent: US6451968, 2002, B1, .
[15] Patent: US5977296, 1999, A, .
[16] Patent: US5539082, 1996, A, .
[17] Patent: US5719262, 1998, A, .
[18] Patent: EP804456, 2002, B1, .
[19] Patent: EP804456, 2002, B1, .
[20] Patent: US6228982, 2001, B1, .
[21] Patent: US6710164, 2004, B1, .
[22] Patent: US6713602, 2004, B1, .
  • 2
  • [ 105-39-5 ]
  • [ 66224-66-6 ]
  • [ 25477-96-7 ]
References: [1] European Journal of Medicinal Chemistry, 2008, vol. 43, # 12, p. 2778 - 2783.
  • 3
  • [ 66224-66-6 ]
  • [ 870281-82-6 ]
References: [1] Patent: WO2016/108206, 2016, A2, .
 

Historical Records

Categories