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CAS No. :	1396337-93-1
Formula :	C₁₁H₈N₄O
M.W :	212.21
SMILES Code :	N#CC1=NC(C)=CC(OC2=CN=CN=C2)=C1

Yield	Reaction Conditions	Operation in experiment
82.1%	With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 80℃; for 36h;Large scale;	To a solution of 5-hydroxypyrimidine (9, 1.73 kg, 18.08 mol) in DMF (23.0 L,10 V), potassium carbonate (6.25 kg, 45.21 mol) was added followed by <strong>[104711-65-1]4-chloro-6-methylpicolinonitrile</strong> (8, 2.3 kg, 15.07 mol) at 25-30 C. The reactionmass was heated at 75-80 C for 36 h. The reaction was monitored by HPLC 8NMT 2.0% by HPLC). Reaction mass was cooled to 25-30 C. The solid wasfiltered and washed the solid with DMF (4.6 L, 2.0 V). The filtrate was cooled to0-5 C and purified water (27.6 L, 12 V) was added drop wise over a period of1 h. The solid precipitated was filtered and washed with purified water (2.3 L,10 V) to afford 10 as off white solid (2.62 kg, 82.1%). 1H NMR (400 MHz, DMSOd6)d 9.17 (s, 1H), 8.85 (s, 2H), 7.74 (d, J = 2.4 Hz, 1H), 7.32 (d, J = 2.3 Hz, 1H),2.48 (s, 3H); 13C NMR (100 MHz, DMSO-d6) d = 164.04, 162.28, 155.51, 150.02,148.75, 133.54, 117.05, 115.59, 115.04, 23.82 ppm; LCMS (Method 1):RT = 0.535 min, m/z = 213.2 [M+H]+; HRMS, calc?d for C11H8N4O [M],212.0698; found 212.0697.
77%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h;	d. PREPARATION OF 6-METHYL-4-(PYRIMIDIN-5-YLOXY)PICOLINONITRILE.[00399] <strong>[104711-65-1]4-chloro-6-methylpicolinonitrile</strong> (4.0 g, 26 mmol, 1.0 eq), 5-hydroxypyrimidine (5.56 g, 57.9 mmol, 2.20 eq), K2C03 (7.24 mg, 52.4 mmol, 2.0 eq) and DMF (66 mL) were added to a reaction vessel and heated at 80 C for 16 hours. The reaction was filtered and concentrated on silica gel (25 g). The silica gel was loaded on top of a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude solid was purified by flash chromatography on silica gel to afford 4.31 g (77%) of the title compound as a pale-yellow solid. NMR (400 MHz, DMSO-<¾) delta 9.1 7 (s, 1 H), 8.85 (s, 2H), 7.74 (d, J = 2.4 Hz, 1 H), 7.32 (d, J = 2.3 Hz, 1 H), 2.48 (s, 3H); ES-MS [M+l ]+: 213.2.

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P232	Protect from moisture.
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P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
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P320
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P321
P322
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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

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CAS No.: 1396337-93-1

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CAS No.: 1396337-93-1

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[ 1396337-93-1 ] Synthesis Path-Downstream 1~1

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