1,3-Benzoxazol-6-amine → N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amine

HRID 1912649Notes

Reaction equation

HRID 1912649 reaction equation
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:23]1[C:27]2[CH:28]=[C:29]([NH2:32])[CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1.C(O[Na])(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:1]([O:8][C:9]1[C:10]([NH:32][C:29]2[CH:30]=[CH:31][C:26]3[N:25]=[CH:24][O:23][C:27]=3[CH:28]=2)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5841201,3-Benzoxazol-6-amineHCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidineHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 66958358N-(5-(benzyloxy)-6-p-tolylpyrimidin-4-yl)benzo[d]oxazol-6-amineYield 25.9%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

5-(benzyloxy)-4-chloro-6-p-tolylpyrimidine (50 mg, 0.161 mmol) was dissolved in PhMe, to this was added benzo[d]oxazol-6-amine (23.7 mg, 1.1 eq), Pd(dba)2 (4.6 mg, 0.05 eq), t-BuONa (31 mg, 2 eq), and (±)-BINAP (15 mg, 0.15 eq). The mixture was degassed and heated at 115° C. overnight. The mixture was cooled to room temperature, diluted with EtOAc and washed with H2O. Preparative TLC gave 17 mg of the title compound.

Workup

  1. customThe mixture was degassed
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with EtOAc
  4. washwashed with H2O

Sources & evidence

ORD record
ord-72bc7667b5d54a25b34032e2f8cef03b
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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