Benzenamine, 3-ethynyl- → HCID 86757703, compound

HRID 1249739Notes

Reaction equation

HRID 1249739 reaction equation
CS[C:3]1[C:12]2[C:7]([CH:8]=[N:9][CH2:10][N:11]=2)=[CH:6][C:5]2=[N:13][CH:14]=[N:15][C:4]=12.[C:16]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21])#[CH:17].[ClH:25].N1C=CC=CC=1>C(O)(C)(C)C>[ClH:25].[C:16]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH:21][CH:6]1[C:7]2[N:8]=[CH:9][N:10]=[CH:11][C:12]=2[CH:3]=[C:4]2[N:15]=[CH:14][N:13]=[C:5]12)#[CH:17]

Participants

5

Reactant 3

HCID 104682Benzenamine, 3-ethynyl-HCID 10176127Pyridinium chlorideHCID 18184410HCID 18184410, compound

Product 1

HCID 86757703HCID 86757703, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 4-methylthio-6H-imidazo[4,5-g]quinazoline (0.0455 g, 0.210 mmol), prepared as described in Leonard, N. J.; Morrice, A. G.; Sprecker, M. A., J. Org. Chem., 1975, 40 (3), 356-363, 3-ethynylaniline (0.0672 g, 0.574 mmol) and pyridine hydrochloride (0.0274 g, 0.237 mmol) in t-butanol (5 mL) was heated to reflux for 6 hours then cooled to room temperature. Precipitate was collected and washed with t-butanol to give 4-(3-ethynylanilino)-imidazo[4,5-g]-quinazoline hydrochloride as a yellow solid: 0.0349 g (58%); 1H NMR (DMSO-d6) δ4.34 (1H, s), 7.48 (1H, m), 7.53 (1H, m), 7.82 (1H, m), 7.98 (1H, s), 8.13 (1H, s), 8.81 (1H, s), 8.99 (1H, s), 9.24 (1H, s), 11.49 (1H, br s ); m/e 286 (M+1).

Workup

  1. customprepared
  2. temperatureto reflux for 6 hours
  3. customPrecipitate was collected
  4. washwashed with t-butanol

Sources & evidence

ORD record
ord-89793f5c20f744abacb13e4c659122e5
Source dataset
uspto-grants-2002_01
Patent number
US06335344B1

Reaction notes

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