3438-47-9

Basic information

• Product Name: Pyrimidine, 4-(1,1-dimethylethyl)- (9CI)
• Synonyms: Pyrimidine, 4-(1,1-dimethylethyl)- (9CI);4-tert-Butyl-pyrimidine
• CAS NO: 3438-47-9
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19428
• Product Categories: PYRIMIDINE
• Mol File: 3438-47-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyrimidine, 4-(1,1-dimethylethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 4-(1,1-dimethylethyl)- (9CI)(3438-47-9)
• EPA Substance Registry System: Pyrimidine, 4-(1,1-dimethylethyl)- (9CI)(3438-47-9)

Safety Data

• Hazardous Substances Data: 3438-47-9(Hazardous Substances Data)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 3473-63-0 formamidine acetic acid 
• 82619-56-5 1-Benzyl-4-t-butylpyrimidinium bromide 

Downstream Products

• 3438-49-1 4-tert-butyl-6(1H)-pyrimidone 
• 17321-94-7 2-amino-4-(trifluoromethyl)pyrimidine 
• 3435-27-6 6-tert-butylpyrimidin-4-ylamine 
• 82619-56-5 1-Benzyl-4-t-butylpyrimidinium bromide 

Relevant articles and documents

Substituted triazines and pyrimidines from 1,3,5-triazine and a lithium amidinate, alkyl- or 1-azaallyl

Treatment of 1,3,5-triazine 1 with an alkyllithium LiR [R = a Me, b Bun, c But, d Ph, e CH2TMS, f CH(TMS)2 or g Si(TMS)3(THF)3] yielded the appropriate 1 : 1 addition product 2a-2g, which upon hydrolysis gave the corresponding mono-substituted dihydro-1,3,5-triazine HNC(H)NC(H)(R)NCH 3a-3g. 1H NMR spectral data showed that the 1,4-dihydrotriazine 3f in toluene-d8 was in equilibrium with its 1,2-dihydro tautomer. Heating 3f with EtOH or H2O in an acidic medium led to the facile cleavage of a C-Si bond and the formation of EtOTMS or (TMS)2O, respectively. The 13C and 15N NMR spectral data are compared with those obtained by B3LYP/6-31+G* computations on the model compound NC(H)NCH2NCH. Treatment of 1 with the lithium amidinate [Li{N(TMS)C(Ph)NTMS}]2 or with 1-azaallyllithium [Li{N(TMS)C(Ph)C(H)TMS}(tmen)], [Li{N(TMS)C(BUt)C(H)TMS}]2 or [Li{N(TMS)C(Ph)C(TMS)2}(THF)2] yielded 2-phenyltriazine 5, 4-phenylpyrimidine 6, 4-tert-butylpyrimidine 9 or, in poor yield, the new 4-phenyl-5-trimethylsilylpyrimidine 7, respectively. In the case of 1 and [Li{N(TMS)C(BUt)C(H)TMS}]2 an intermediate was isolated - the thermally unstable [Li{N(TMS)C(H)NC(H)NC(H)C(H)C(BUt)NTMS}]n 8. A pathway is proposed involving the 1,4-addition of the lithium compound to 1,3,5-triazine 1, followed by a 1,3-trimethylsilyl shift, ring-opening and the formation of a new C-C or C-N bond to form the appropriate aromatic heterocycle.

On the Reactivity of N-Benzylpyrimidinium Salts with Nitrogen Nucleophiles (1,2)

Treatment of the 1-benzyl salts of pyrimidine, 4,6-dimethylpyrimidine, and 4-t-butylpyrimidine with liquid ammonia leads to debenzylation.The 1H-nmr spectroscopic evidence is presented that the initial step in the debenzylation of 1-benzyl-4,6-dimethylpyrimidinium bromide is the addition of the ammonia at C-2, while with 1-benzyl-4-t-butylpyrimidinium bromide the addition takes place at C-6.It is proved by 15N labelling that the debenzylation occurs according to the ANRORC mechanism.The above-mentioned 1-benzylpyrimidinium bromides give with hydrazine, pyrazole, 3,5-dimethylpyrazole and 3-t-butylpyrazole, respectively.