Carbon tetrabromide → HCID 67258656, compound

HRID 1476632Notes

Reaction equation

HRID 1476632 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[N:10]=[C:9]([CH2:11]O)[O:8][N:7]=1)[CH2:2][CH3:3].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:37]=[C:38]1[NH:43][C:42]2[CH:44]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[S:46][C:41]=2[C:40](=[O:53])[N:39]1[CH:54]1[CH2:59][CH2:58][N:57]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:56][CH2:55]1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CN(C=O)C>[O:37]=[C:38]1[N:43]([CH2:11][C:9]2[O:8][N:7]=[C:6]([CH2:5][O:4][CH2:1][CH2:2][CH3:3])[N:10]=2)[C:42]2[CH:44]=[C:45]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[S:46][C:41]=2[C:40](=[O:53])[N:39]1[CH:54]1[CH2:59][CH2:58][N:57]([C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:56][CH2:55]1

Participants

8

Reactant 5

HCID 11205Carbon tetrabromideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 63758128HCID 63758128, compoundHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Product 1

HCID 67258656HCID 67258656, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(propoxymethyl)-1,2,4-oxadiazol-5-yl]methanol (250 mg, compound D22) and CBr4 (620 mg) in DCM (5 ml) are added triphenylphosphine (490 mg) and the reaction mixture is stirred for 15 min at RT. This solution is added to a stirred suspension of tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (0.5 g; compound B50) and potassium carbonate (323 mg) in DMF and the reaction mixture is stirred for 3 h at 65° C. Afterwards the solvent is removed under vacuo, the resulting residue is treated with EtOAc/cyclohexane (1:1) and the suspension is filtered. The filtrate is purified by flash chromatography (silica gel, eluent EtOAc/cyclohexane 1:1) and the product fraction are washed with diethylether to give the title compound as a solid.

Workup

  1. stirringthe reaction mixture is stirred for 3 h at 65° C
  2. customAfterwards the solvent is removed under vacuo
  3. additionthe resulting residue is treated with EtOAc/cyclohexane (1:1)
  4. filtrationthe suspension is filtered
  5. customThe filtrate is purified by flash chromatography (silica gel, eluent EtOAc/cyclohexane 1:1)
  6. washthe product fraction are washed with diethylether

Sources & evidence

ORD record
ord-98fddceeaea447e38ee9832be020f088
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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