31375-19-6

Basic information

• Product Name: Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI)
• Synonyms: Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI);Pyrimido[4,5-d]pyrimidine, 1,4-dihydro-7-methyl-
• CAS NO: 31375-19-6
• Molecular Formula: C₇H₈N₄
• Molecular Weight: 148.16522
• Product Categories: PYRIMIDINE
• Mol File: 31375-19-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 173 °C (decomp)
• Boiling Point: 277.008°C at 760 mmHg
• Flash Point: 121.33°C
• Appearance: /
• Density: 1.397g/cm3
• PKA: 8.73±0.20(Predicted)
• CAS DataBase Reference: Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI)(31375-19-6)
• EPA Substance Registry System: Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI)(31375-19-6)

Safety Data

• Hazardous Substances Data: 31375-19-6(Hazardous Substances Data)

Usage

General Description

Pyrimido[4,5-d]pyrimidine, 1,5-dihydro-2-methyl- (6CI,8CI,9CI) is a complex organic compound that belongs to the group of Pyrimidines and their derivatives, which are aromatic compounds containing one or more Pyrimidine rings. In a pyrimidine ring, two Nitrogen atoms along with four Carbon atoms are interlinked to form a heterocyclic aromatic ring structure. The abbreviation (6CI,8CI,9CI) suggests its three different conformers, differing each other by the orientation of its functional groups. The presence of a Methyl group, i.e., a Carbon atom linked to three Hydrogen atoms, denotes its additional organic property. However, specific information regarding its characteristics like solubility, reactivity, applications, and safety measures are typically documented by chemical database and scientific references.

Synthetic route

5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6)

Conditions	Yield
1.) 80 to 85 deg C, 2.) 90 deg C, 30 min;	88.5%

5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) + orthoformic acid triethyl ester (122-51-0) → 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6)

Conditions	Yield
With toluene-4-sulfonic acid Heating;	71%

pyridine (110-86-1) + 4-Amino-2-methyl-5-thioformamidomethylpyrimidin (31375-20-9) → 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6)

4-Amino-2-methyl-5-thioformamidomethylpyrimidin (31375-20-9) → 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6)

Conditions	Yield
With pyridine

5-(aminomethyl)-2-methylpyrimidin-4-amine (95-02-3) → 3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O 2: pyridine View Scheme

3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6) + 3-Mercapto-4-oxopentyl Acetate (55289-66-2) → Thiamine formate (130967-53-2)

Conditions	Yield
With formic acid for 0.5h; Ambient temperature;	89.3%

3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6) → 2-methyl-4-amino-5-formylaminomethylpyrimidine (1886-34-6)

Conditions	Yield
an der Luft erfolgt;

3,4-Dihydro-7-methylpyrimido<4,5-d>pyrimidine (31375-19-6) + 3-Mercapto-4-oxopentyl Acetate (55289-66-2) → Thiamine hydrochloride (67-03-8)

Conditions	Yield
With hydrogenchloride; formic acid 1.) 30 min, RT, 2.) EtOH, 30 min, RT; Yield given. Multistep reaction;

Upstream product

• 95-02-3 5-(aminomethyl)-2-methylpyrimidin-4-amine 
• 122-51-0 orthoformic acid triethyl ester 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 31375-20-9 4-Amino-2-methyl-5-thioformamidomethylpyrimidin 
• 110-86-1 pyridine 

Downstream Products

• 67-03-8 Thiamine hydrochloride 
• 1886-34-6 2-methyl-4-amino-5-formylaminomethylpyrimidine 

Relevant articles and documents

127. A new convergent synthesis of thiamine hydrochloride

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