Methylamine → 4-Amino-2-methylamino-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline

HRID 727216Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH2:8][CH2:7][C:6]=2[N:5]=[C:4](S(C)=O)[N:3]=1.[CH3:22][NH2:23]>C(O)C>[NH2:1][C:2]1[C:11]2[CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([NH:23][CH3:22])[N:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A suspension of 1.6 grams (0.005 mole) of 4-amino-2-methylsulfinyl-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline (prepared as in Example 17) and 10 mL of aqueous 40% methylamine in 50 mL of ethanol is placed in a glass tube, which is then sealed. The sealed tube is heated at about 180° C. for 7 hours and then is cooled in an ice-bath and opened. The reaction mixture is concentrated under reduced pressure to a residue. The residue is stirred with an aqueous 10% potassium carbonate solution, and the resultant suspension is extracted with chloroform. The extract is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel, yielding 4-amino-2-methylamino-6-(2-chlorophenyl)-5,6,7,8-tetrahydroquinazoline.

Workup

customis placed in a glass tube
customwhich is then sealed
temperatureis cooled in an ice-bath
concentrationThe reaction mixture is concentrated under reduced pressure to a residue
extractionthe resultant suspension is extracted with chloroform
dry with materialThe extract is dried with magnesium sulfate
filtrationfiltered
concentrationThe filtrate is concentrated under reduced pressure to a residue

Sources & evidence

ORD record: ord-52567418102e42e09b54f198e3ae5fe6
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712281

Reaction notes

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