Bromobenzene → HCID 59652734, compound

HRID 1662849Notes

Reaction equation

HRID 1662849 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[K+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[N+:1]([C:4]1[CH:5]=[N:6][C:7]([NH:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 764905-Nitropyrimidin-2-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23665647Potassium tert-butoxide

Product 1

HCID 59652734HCID 59652734, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-nitro-pyrimidin-2-ylamine (0.10 g, 0.71 mmol), bromobenzene (0.15 g, 0.96 mmol), Pd(OAc)2 (13 mg, 0.057 mmol), Xantphos (67 mg, 0.12 mmol) and potassium tert-butoxide (0.22 g, 2.0 mmol) in DMF (3 mL) was sealed in a microwave reaction tube and irradiated with microwave at 140° C. for 15 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the crude product used in the next step without further purification.

Workup

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 140° C. for 15 min
  3. customthe cap was removed
  4. filtrationthe resulting mixture filtered
  5. washthe filtered solid washed with DCM
  6. concentrationThe filtrate was concentrated
  7. customthe crude product used in the next step without further purification

Sources & evidence

ORD record
ord-3431d7ddad0944968e75966b3171fc20
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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