2-Aminopyrimidine → 2-Isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine

HRID 907414Notes

Reaction equation

C(Cl)(=O)[C:2](Cl)=[O:3].[NH2:7][C:8]1[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[CH:11]=[C:10]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[N:9]=1.NC1N=CC=CN=1>O1CCOCC1>[N:7]([C:8]1[N:9]=[C:10]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])[CH:11]=[C:12]([O:14][CH2:15][C:16]([F:18])([F:19])[F:17])[N:13]=1)=[C:2]=[O:3]

Participants

Conditions

Temperature: 90 °C

Procedure

Oxalyl chloride (42.0 mL, 481 mmol) was dissolved in anhydrous 1,4-dioxane (400 mL) under an N2 atmosphere. The resulting solution was heated to 90° C. To the hot solution was slowly added a solution of 2-amino-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (14.0 g, 48 mmol) in anhydrous 1,4-dioxane (50 mL). After addition of the aminopyrimidine solution was complete, heating was continued for 6 h, the heat removed, and the solution cooled to room temperature. The solution was concentrated and the residue distilled at reduced pressure to afford the product as a clear oil (12.4 g, 82% yield): bp 53-54° C. (ca.0.1 to 0.2 mm Hg): 1H NMR (CDCl3) δ 6.19 (s, 1H), 4.82-4.74 (q, 2H, J=8.2 Hz).

Workup

temperatureheating
customthe heat removed
temperaturethe solution cooled to room temperature
concentrationThe solution was concentrated
distillationthe residue distilled at reduced pressure

Sources & evidence

ORD record: ord-ab6ffd51323045d3872e78e5ee1e2e5d
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013154B2

Reaction notes

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