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

HRID 1917270Notes

Reaction equation

HRID 1917270 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-f18dce8c46714e049d74c18bb693676a
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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