Methanol → HCID 68388889, compound

HRID 927309Notes

Reaction equation

HRID 927309 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([N:26]3[CH2:31][CH2:30][N:29]([C:32]4[N:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[CH2:28][CH2:27]3)=[O:25])[CH:19]=1)[C:14](=[O:38])[NH:13][C:12]2=[O:39].CO.[NH4+].[Cl-]>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([N:26]3[CH2:27][CH2:28][N:29]([C:32]4[N:33]=[CH:34][CH:35]=[CH:36][N:37]=4)[CH2:30][CH2:31]3)=[O:25])[CH:19]=1)[C:14](=[O:38])[NH:13][C:12]2=[O:39]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 68388787HCID 68388787, compound

Product 1

HCID 68388889HCID 68388889, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (4N in DCM, 10 mL, 40 mmol) was added dropwise to a mixture of 8-methoxy-1-(3-(4-(pyrimidin-2-yl)piperazine-1-carbonyl)benzyl)quinazoline-2,4(1H,3H)-dione (60 mg, 0.13 mmol) in DCM (25 mL) at −70° C. The mixture was warmed to room temperature and stirred at r.t overnight. After cooled at ice-bath, 10 mL MeOH was added dropwise and then NH4Cl (a.q.) was added. The mixture was extracted by DCM (50 mL×2), the combined organic layer was dried to give crude product which was purified by TLC (DCM/MeOH=20:1) to give the target product (7.64 mg, 13.1% yield). 1H NMR (DMSO-d6): 11.64 (s, 1H), 10.34 (s, 1H), 8.36 (d, J=4.8 Hz, 2H), 7.51 (dd, J=6.8 and 2.6 Hz, 1H), 7.39-7.34 (m, 1H), 7.27-7.23 (m, 3H), 7.10-7.03 (m, 2H), 6.65 (t, J=4.7 Hz, 1H), 5.63 (s, 2H), 3.85-3.53 (m, 8H). MS: m/z 459.4 [M+H]+.

Workup

  1. temperatureAfter cooled at ice-bath
  2. extractionThe mixture was extracted by DCM (50 mL×2)
  3. customthe combined organic layer was dried
  4. customto give crude product which
  5. customwas purified by TLC (DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-df8ba9096ed347c797ea090eb42de4c2
Source dataset
uspto-grants-2016_03
Patent number
US09290460B2

Reaction notes

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