2-t-Butyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine → 2-t-Butyl-5-(aminomethyl)oxazoline

HRID 2082433Notes

Reaction equation

[C:1]([C:5]1[NH:6][CH2:7][CH:8]([OH:11])[CH2:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([C:5]1[O:11][CH:8]([CH2:7][NH2:6])[CH2:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

Solid 2-t-butyl-5-hydroxy-1,4,5,6-tetrahydropyrimidine (2.55 g, 1.63 mmol) was heated to reflux in 100 mL of toluene for 22 hours. The solution was cooled to 25° C. and the slurry was filtered to remove 0.91 g of unconverted tetrahydropyrimidine after drying. The toluene filtrate was evaporated to give 1.17 g of 2-t-butyl-5-(aminomethyl)oxazoline as an oil: 1H NMR (CDCl3) δ 4.5 (m, 1H), 3.8 (apparent dd, 1H), 3.5 (apparent dd, 1H), 2.8 (apparent dq, 2H), 1.2 ppm (s, 9H), 13C NMR {1H} (CDCl3) δ 173.3 (1 C), 80.1 (1 C), 56.4 (1 C), 45.3 (1 C), 32.5 (1 C), 27.1 ppm (3 C). The neat oil gradually solidifies over a number of days, even at 0° C., reverting back to the tetrahydropyrimidine.

Workup

filtrationthe slurry was filtered
customto remove 0.91 g of unconverted tetrahydropyrimidine
customafter drying
customThe toluene filtrate was evaporated

Sources & evidence

ORD record: ord-cfb80a88be3548909b4b3066bc0e8908
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189166

Reaction notes

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