Diisobutylaluminumhydride → HCID 17990112, compound

HRID 1292960Notes

Reaction equation

HRID 1292960 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:35][CH2:34][C:9]2[C:10]3[C:15]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=5)=[C:19]([Cl:32])[CH:18]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:33][C:8]=2[CH2:7]1)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:32][C:19]1[CH:18]=[C:17]([NH:16][C:15]2[C:10]3[C:9]4[CH2:34][CH2:35][CH:6]([CH2:5][CH2:4][OH:3])[CH2:7][C:8]=4[S:33][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 58774533HCID 58774533, compound

Product 1

HCID 17990112HCID 17990112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (40 mL) was added 7 g (13.3 mmol, 1 equiv) of {4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-7-yl}-acetic acid ethyl ester. A 1M solution of diisobutylaluminum hydride in hexanes (53 mL, 53 mmol, 4 equiv) was added to the solution and the reaction was stirred at rt for 3 h. The reaction mixture was quenched with Rochelle's salt followed by EtOAc. The solution was separated and the aqueous layer discarded and the organic layer was washed with brine (100 mL) and water (100 mL). The resulting material 5.5 g (85%)was pure white solid of Example 137. 1H-NMR (DMSO-d6) δ 1.5 (m, 3H), 1.95 (m, 2H), 2.93 (dd,1H), 3.16 (2H), 3.53 (m,2H), 4.45 (t, 1H), 5.2 (s, 2H), 7.17 (m, 2H), 7.28 (m,2H), 7.43 (m, 1H), 7.5 (dd, 2H), 7.76 (dd, 1H), 8.05 (s, 1H). LCMS RT=3.46 min; [M+H]+=484.2.

Workup

  1. customThe reaction mixture was quenched with Rochelle's salt
  2. customThe solution was separated
  3. washthe organic layer was washed with brine (100 mL) and water (100 mL)

Sources & evidence

ORD record
ord-ef39709c43464033a687920fbbdfe057
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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