51991-94-7|5-Oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid| Ambeed

CAS No. :	51991-94-7
Formula :	C₇H₄N₂O₃S
M.W :	196.18
SMILES Code :	O=C(C1=CN=C(SC=C2)N2C1=O)O
MDL No. :	MFCD03011512
InChI Key :	FDGPDTWORUVKQX-UHFFFAOYSA-N
Pubchem ID :	762362

Safety of [ 51991-94-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 51991-94-7 ]

* 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.

Downstream synthetic route of [ 51991-94-7 ]

[ 51991-94-7 ] Synthesis Path-Downstream 1~54

1
[ 51991-94-7 ]
[ 32278-54-9 ]

References: [1]Journal of Organic Chemistry,1959,vol. 24,p. 787,792.
[2]Journal of the Chemical Society C: Organic,1971,p. 2094 - 2097.

2
[ 32278-52-7 ]
[ 51991-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;	(b) 5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid A mixture of ethyl 5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxylate (11.2g., 50mM) and 2N hydrochloric acid (75ml) was heated under reflux for 5 hours. The reaction mixture was cooled and filtered to give the required product in 79.7% weight yield (7.81g). numax (KBr disc) 1720 (acid C=O)cm-1; lambdamax (NaHCO3 solution) 232nm (epsilonm 2650), 263nm (epsilonm 2030), 328nm (epsilonm 6000) and 339nm (epsilonm 5400); (Found: C, 43,65; H, 2.26; N, 14.16; S, 16.62%. C7 H4 N2 O3 S requires C, 43.87; H, 2.06; N, 14.28; S, 16.32%.

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.
[2]Journal of Organic Chemistry,1959,vol. 24,p. 787,792.
[3]Journal of the Chemical Society C: Organic,1971,p. 2094 - 2097.
[4]Patent: US4081545,1978,A .

3
[ 51991-90-3 ]
[ 51991-94-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1974,vol. 22,p. 243 - 247.

4
[ 65692-03-7 ]
[ 51991-94-7 ]

References: [1]Chemical and pharmaceutical bulletin,1977,vol. 25,p. 3360 - 3365.

5
[ 110-89-4 ]
[ 51991-94-7 ]
[ 106695-59-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

6
[ 110-91-8 ]
[ 51991-94-7 ]
[ 106695-60-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

7
[ 109-01-3 ]
[ 51991-94-7 ]
[ 106695-61-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

8
[ 96-50-4 ]
[ 51991-94-7 ]
[ 106695-67-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

9
[ 504-29-0 ]
[ 51991-94-7 ]
[ 106695-68-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

10
[ 1072-67-9 ]
[ 51991-94-7 ]
[ 106695-66-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

11
[ 92-54-6 ]
[ 51991-94-7 ]
[ 106695-62-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

12
[ 67-56-1 ]
[ 51991-94-7 ]
[ 106695-50-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

13
[ 71-23-8 ]
[ 51991-94-7 ]
[ 106695-52-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

14
[ 51991-94-7 ]
[ 107-03-9 ]
[ 106695-56-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

15
[ 51991-94-7 ]
[ 64-17-5 ]
[ 106695-51-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

16
[ 51991-94-7 ]
[ 109-79-5 ]
[ 106695-57-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

17
[ 51991-94-7 ]
[ 109-86-4 ]
[ 106695-54-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

18
[ 51991-94-7 ]
[ 1135-14-4 ]
[ 106695-65-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

19
[ 51991-94-7 ]
[ 108-98-5 ]
[ 106695-58-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

20
[ 51991-94-7 ]
[ 106695-49-2 ]
[ 106695-69-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

21
[ 51991-94-7 ]
[ 62-53-3 ]
[ 106695-63-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

22
[ 51991-94-7 ]
[ 67-63-0 ]
[ 106695-53-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

23
[ 51991-94-7 ]
[ 121-50-6 ]
[ 106695-64-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

24
[ 51991-94-7 ]
[ 108-95-2 ]
[ 106695-55-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

25
[ 51991-94-7 ]
[ 76661-92-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.
[2]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

27
[ 97545-54-5 ]
[ 51991-94-7 ]

References: [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 754 - 757.

28
[ 51991-94-7 ]
5-oxo-N-(1,3-thiazol-2-yl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

29
[ 51991-94-7 ]
5-oxo-N-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

30
[ 51991-94-7 ]
ethyl-2-[[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl)carbonyl]amino]acetate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

31
[ 51991-94-7 ]
methyl-2-[[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl)carbonyl]amino]propanoate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

32
[ 51991-94-7 ]
6-[(4-methyl-1-piperazinyl)carbonyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

33
[ 51991-94-7 ]
methyl (4s)-3-[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl)carbonyl]-1,3-thiazolidine-4-carboxylate [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

34
[ 51991-94-7 ]
N-[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl)carbonyl]-L-phenylalanine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

35
[ 51991-94-7 ]
N-[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl)carbonyl]-S-(+)-trityl-L-cysteine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2000,vol. 37,p. 95 - 101.

36
[ 51991-94-7 ]
[ 106695-47-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

37
[ 51991-94-7 ]
[ 106695-46-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 345 - 346.

38
[ 51991-94-7 ]
1-(2-tert-butylphenyl)piperazine dihydrochloride [ No CAS ]
[ 1252655-66-5 ]

Yield	Reaction Conditions	Operation in experiment
47%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃;	Example 12 6-[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (500 mg), <strong>[51991-94-7]5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid</strong> (371 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (395 mg), 1-hydroxy-1H-benzotriazole monohydrate (315 mg), triethylamine (0.558 mL), and N,N-dimethylformamide (10 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (320 mg, 47%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) delta 1.42 (s, 9H), 2.65-2.72 (m, 1H), 2.78-2.99 (m, 4H), 3.30-3.32 (m, 1H), 3.65-3.69 (m, 1H), 4.53-4.56 (m, 1H), 7.13-7.16 (m, 1H), 7.20-7.25 (m, 1H), 7.30-7.38 (m, 2H), 7.66 (d, J=4.8 Hz, 1H), 8.15 (d, J=4.8 Hz, 1H), 8.21 (s, 1H).

References: [1]Patent: US2012/71489,2012,A1 .Location in patent: Page/Page column 67.

39
[ 111-49-9 ]
[ 51991-94-7 ]
6-(azepane-1-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

40
[ 123-90-0 ]
[ 51991-94-7 ]
6-(thiomorpholine-4-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

41
[ 503-29-7 ]
[ 51991-94-7 ]
6-(azetidine-1-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

42
[ 51991-94-7 ]
[ 929-06-6 ]
N-(2-(2-hydroxyethoxy)ethyl)-5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

43
[ 16153-81-4 ]
[ 51991-94-7 ]
N-[4-(4-methylpiperazine-1-yl)phenyl]-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

44
[ 51991-94-7 ]
[ 148546-99-0 ]
N-[3-(4-methylpiperazine-1-yl)phenyl]-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

45
[ 51991-94-7 ]
[ 14691-88-4 ]
(2,2,6,6-tetramethyl-4-[(5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-yl)carbonyl]amino}piperidin-1-yl)oxidanyl [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

46
[ 51991-94-7 ]
[ 57260-73-8 ]
C₁₄H₁₈N₄O₄S [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

47
[ 110-89-4 ]
[ 51991-94-7 ]
6-(piperidine-1-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

48
[ 193269-78-2 ]
[ 51991-94-7 ]
C₁₅H₁₈N₄O₄S [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

49
[ 110-91-8 ]
[ 51991-94-7 ]
6-(morpholine-4-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

50
[ 123-75-1 ]
[ 51991-94-7 ]
6-(pyrrolidine-1-carbonyl)-5H-thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

51
[ 109-01-3 ]
[ 51991-94-7 ]
6-[(4-methyl-1-piperazinyl)carbonyl]-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

52
[ 38212-30-5 ]
[ 51991-94-7 ]
6-[4-(4-methoxyphenyl)piperazine-1-yl]carbonyl}-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

53
[ 51991-94-7 ]
[ 30459-17-7 ]
6-({4-[4-(trifluoromethyl)phenyl]piperazine-1-yl}carbonyl)-5H-[1,3]thiazolo[3,2-a]pyrimidine-5-one [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

54
[ 51991-94-7 ]
N-(1-(4-methoxyphenyl)piperidin-4-yl)-5-oxo-5H-thiazolo[3,2-a]pyrimidine-6-carboxamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 14915 - 14925.

Historical Records

Technical Information

• Acyl Group Substitution • Arndt-Eistert Homologation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hunsdiecker-Borodin Reaction • Hydride Reductions • Lawesson's Reagent • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Ugi Reaction

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Code	Phrase
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P321
P322
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P378
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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.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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Storage
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P401
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Disposal
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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
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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
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Health hazards
Code	Phrase
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
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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.: 51991-94-7

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CAS No.: 51991-94-7

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[ 51991-94-7 ] Synthesis Path-Downstream 1~54

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