2,6-Di-tert-butylpyridine → HCID 136337164, compound

HRID 1428833Notes

Reaction equation

HRID 1428833 reaction equation
C(C1C=CC(N)=CC=1)#C.C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.Cl[C:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[C:32]([N:37]1[CH:41]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:39]=[N:38]1)[NH:31][C:30]2=[O:47])=[CH2:26]>>[C:25]([C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[C:32]([N:37]1[CH:41]=[C:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:39]=[N:38]1)[NH:31][C:30]2=[O:47])#[CH:26]

Participants

4

Reactant 3

HCID 685102,6-Di-tert-butylpyridineHCID 37600254-EthynylanilineHCID 136337165HCID 136337165, compound

Product 1

HCID 136337164HCID 136337164, compound

Procedure

The titled compound was prepared in a manner analogous to Example 27, steps C-D, using 4-ethynylaniline in step C, and with the addition of 4.0 equivalents of 2,6-di-tert-butylpyridine in step D. The crude product contained a 2.4:1 mixture of the titled product and 1-[6-(1-chloro-vinyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, ethyl ester. A portion of this mixture was purified by HPLC to afford 1-(6-ethynyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid, ethyl ester. MS (ESI): mass calcd. for C16H12N4O3, 308.1; m/z found, 309.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.98 (br s, 1H), 8.95 (s, 1H), 8.27 (s, 1H), 8.07 (s, 1H), 7.82 (dd, J=8.4, 1.9 Hz, 1H), 7.72-7.54 (m, 1H), 4.31 (s, 1H), 4.23 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 3H).

Workup

  1. customThe titled compound was prepared in a manner analogous to Example 27, steps C-D
  2. customA portion of this mixture was purified by HPLC

Sources & evidence

ORD record
ord-83c4c17c3981489d814659ef3c5a3fc8
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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