Dichloromethane → HCID 23634344, compound

HRID 2039673Notes

Reaction equation

HRID 2039673 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:3]=1.[C:12]([N:19]1[CH:23]=NC=N1)(N1C=NC=N1)=[O:13].NC1[CH:39]=[CH:38][C:28]([O:29][C:30]2[CH:35]=[CH:34][N:33]=[C:32]([C:36]#[N:37])[CH:31]=2)=[CH:27][C:26]=1[F:40].C(Cl)Cl>ClCCCl.CCOC(C)=O>[C:8]([C:4]1[N:5]=[CH:6][N:7]=[C:2]([NH:1][C:12]([NH:19][C:23]2[CH:39]=[CH:38][C:28]([O:29][C:30]3[CH:35]=[CH:34][N:33]=[C:32]([C:36]#[N:37])[CH:31]=3)=[CH:27][C:26]=2[F:40])=[O:13])[CH:3]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7137446-tert-butylpyrimidin-4-amineHCID 43939611,1'-Carbonyl-di-(1,2,4-triazole)HCID 551566584-(4-Amino-3-fluorophenoxy)picolinonitrile

Product 1

HCID 23634344HCID 23634344, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-amino-4-tert-butylpyrimidine (150.0 mg; 0.99 mmol) in anhydrous 1,2-dichloroethane (1.9 mL) was added 1,1′-carbonyldi(1,2,4-triazole) (195.4 mg, 1.19 mmol, 1.2 eq), and the reaction mixture was stirred at 65° C. for 3 days. A solution of 4-(4-amino-3-fluorophenoxy)pyridine-2-carbonitrile (227.4 mg; 0.99 mmol, 1.0 eq) in anhydrous 1,2-dichloroethane (1.9 mL) was then added, and the reaction mixture was heated at 65° C. for 5 h. The reaction was diluted with EtOAc, and the organic layer was washed with water and brine, dried over sodium sulfate, and evaporated under reduced pressure to give a crude oil. Trituration from DCM afforded the title compound (211 mg, 52%) as a white solid. 1H-NMR (DMSO-d6) δ 10.37 (broad s, 1H), 10.08 (broad s, 1H), 8.75 (d, J=1.2 Hz, 1H), 8.59 (d, J=5.4 Hz, 1H), 8.25 (t, J=9.3 Hz, 1H), 7.73 (d, J=2.7 Hz, 1H), 7.59 (s, 1H), 7.37 (dd, J=12.0, 2.7 Hz, 1H), 7.24 (dd, J=5.4, 2.4 Hz, 1H), 7.08 (ddd, J=9.0, 2.7, 1.5 Hz, 1H), 1.26 (s, 9H); LC-MS m/z 407 [M+H]+, RT=3.17 min.

Workup

  1. temperaturethe reaction mixture was heated at 65° C. for 5 h
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customto give a crude oil

Sources & evidence

ORD record
ord-520bbd72c1e944cf9b24b18d2bcd8028
Source dataset
uspto-grants-2013_11
Patent number
US08580798B2

Reaction notes

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