Carbon tetrabromide → HCID 67258666, compound

HRID 1476634Notes

Reaction equation

HRID 1476634 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH2:7]O.BrC(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:33]=[C:34]1[NH:39][C:38]2[CH:40]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[S:42][C:37]=2[C:36](=[O:49])[N:35]1[CH:50]1[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:52][CH2:51]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH2:7][N:39]1[C:38]2[CH:40]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[S:42][C:37]=2[C:36](=[O:49])[N:35]([CH:50]2[CH2:55][CH2:54][N:53]([C:56]([O:58][C:59]([CH3:61])([CH3:60])[CH3:62])=[O:57])[CH2:52][CH2:51]2)[C:34]1=[O:33]

Participants

8

Reactant 5

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27952184-METHYLOXAZOLE-5-METHANOLHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Product 1

HCID 67258666HCID 67258666, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-methyl-1,3-oxazol-5-yl)methanol (489 mg, compound D26) in dry DCM (0.6 ml) are added tetrabromomethane (1.87 g) and triphenylphosphane (1.48 g) and the mixture is stirred for 1 h at RT. Subsequently the reaction mixture is transferred to a microwave vial and tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (1.00 g, compound B50), dry DMF (150 ml) and potassium carbonate (1.23 g) are added. The mixture is stirred for 4 h at 50° C. and subsequently poured into ice-cold water. After stirring for 5 min the resulting precipitate is filtered off, taken up in EtOAc and dried in vacuo at −78° C. The residue is taken up in EtOAc and dried in vacuo three more times to afford the title compound as a solid.

Workup

  1. additionare added
  2. stirringThe mixture is stirred for 4 h at 50° C.
  3. additionsubsequently poured into ice-cold water
  4. stirringAfter stirring for 5 min the resulting precipitate
  5. filtrationis filtered off
  6. customdried in vacuo at −78° C
  7. customdried in vacuo three more times

Sources & evidence

ORD record
ord-7fe2c7e9bea541a9989b9d703f40c0c8
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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