Tripropylamine → 4-Amino-6-cyclohexanecarboxamidoquinazoline

A mixture of 4,6-diaminoquinazoline hydrochloride (12 g) and tripropylamine (31.7 g) in dry pyridine (120 ml) was stirred in an ice-bath for 1 hour. Cyclohexanecarbonyl chloride (12.1 g) was added dropwise during 4 hours and 20 minutes to the mixture at 70° C. The mixture was stirred for additional 1 hour at 5° C. Crushed ice was added to the reaction mixture. The mixture was stirred for 1 hour and concentrated under reduced pressure. After addition of water, the mixture was adjusted to pH 8 with sodium hydrogen carbonate to give precipitates which were separated by filtration, washed with water and dried. The precipitates were dissolved in a mixture of chloroform and methanol under heating. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give crystalline 4-amino-6-cyclohexanecarboxamidoquinazoline (9.25 g).

1. stirringThe mixture was stirred for additional 1 hour at 5° C
2. additionCrushed ice was added to the reaction mixture
3. stirringThe mixture was stirred for 1 hour
4. concentrationconcentrated under reduced pressure
5. additionAfter addition of water
6. customto give
7. customprecipitates which
8. customwere separated by filtration
9. washwashed with water
10. customdried
11. dissolutionThe precipitates were dissolved in a mixture of chloroform and methanol
12. temperatureunder heating
13. customInsoluble materials were removed by filtration
14. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-8e1332a6bb3c425e804c2101b5d49e5d

Source dataset

uspto-grants-1983_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04377580