Ethyl isocyanate → N-Ethyl-N'-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]urea

HRID 2243040Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1C=[CH:11][C:10]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)=[CH:9][N:8]=1)=[O:5])[CH3:2].CC1(C)C(C)(C)OB(C2C=[N:32]C(N)=NC=2)O1.C(N=C=O)C>>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[N:8]=[CH:9][C:10]([B:13]2[O:14][C:15]([CH3:20])([CH3:21])[C:16]([CH3:18])([CH3:19])[O:17]2)=[CH:11][N:32]=1)=[O:5])[CH3:2]

Participants

Reactant 3

HCID 8022Ethyl isocyanate

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

HCID 592084346-(3-Ethylureido)pyridine-3-boronic acid pinacol ester

Product 1

HCID 57416451N-Ethyl-N'-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]urea

Procedure

The title compound was synthesized by a method analogous to Intermediate 1 synthesis starting with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine and ethyl isocyanate. NMR (CDCl3): 1.23 (t, 3H), 1.32 (s, 12H), 3.41 (m, 2H), 7.95 (s, 1H), 8.76 (s, 2H), 9.10 (s, 1H).

Sources & evidence

ORD record: ord-d569d8bade53423d8f3d502c1b22e059
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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