tert-butyl N-(prop-2-yn-1-yl)carbamate → HCID 57881280, compound

HRID 1817710Notes

Reaction equation

HRID 1817710 reaction equation
C(OC(=O)NCC#C)(C)(C)C.C(O[C:17](=O)[N:18]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[N:24]=[C:23]([CH:34]([CH3:36])[CH3:35])[N:22]=1)C)(C)(C)C>>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]2[N:24]=[C:23]([CH:34]([CH3:36])[CH3:35])[N:22]=[C:21]([CH2:20][NH:18][CH3:17])[CH:26]=2)=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 66616380HCID 66616380, compound

Product 1

HCID 57881280HCID 57881280, compound

Procedure

Prop-2-ynyl-carbamic acid tert-butyl ester was converted to [6-(4-fluoro-phenyl)-2-isopropyl-pyrimidin-4-ylmethyl]-methyl-carbamic acid tert-butyl ester using methods described in Example 112, Step A. This ester was deprotected according to the methods described in Example 1, Step D, to provide the title compound. MS (ESI): exact mass calcd. for C15H18FN3, 259.15; m/z found, 260.3 [M+H]+. 1H NMR (DMSO-d6): 9.45 (s, 2H); 8.31-8.28 (m, 2H), 8.10 (s, 1H), 7.45-7.41 (m, 2H), 4.35 (t, J=6.0, 2H), 3.26-3.18 (m, 1H), 2.69 (t, J=5.4, 3H), 1.37 (d, J=6.9, 6H).

Sources & evidence

ORD record
ord-79445a866cbf4b00854629d8afe7f242
Source dataset
uspto-grants-2009_10
Patent number
US07598255B2

Reaction notes

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