Diisobutylaluminum hydride → HCID 90014767, compound

HRID 930963Notes

Reaction equation

HRID 930963 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([NH:11][C:12]3[C:13]4[C:20]5[CH2:21][CH2:22][CH:23]([C:25](OCC)=[O:26])[CH2:24][C:19]=5[S:18][C:14]=4[N:15]=[CH:16][N:17]=3)=[CH:10][C:4]=2[S:3]1.C([AlH]CC(C)C)C(C)C.[Cl-].[NH4+]>O1CCCC1>[OH:26][CH2:25][CH:23]1[CH2:22][CH2:21][C:20]2[C:13]3[C:12]([NH:11][C:9]4[CH:8]=[CH:7][C:5]5[NH:6][C:2](=[O:1])[S:3][C:4]=5[CH:10]=4)=[N:17][CH:16]=[N:15][C:14]=3[S:18][C:19]=2[CH2:24]1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 118119931HCID 118119931, compound

Product 1

HCID 90014767HCID 90014767, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture comprising 4.42 g (10.36 mmol) (RS)-ethyl 4-[(2-oxo-2,3-dihydro-1,3-benzothiazol-6-yl)amino]-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidine-7-carboxylate (prepared according to example 1) 350 mL tetrahydrofuran and 62.1 mL hydrido(diisobutyl)aluminum (1M in tetrahydrofuran) was stirred at 23° C. overnight. 40 mL saturated ammonium chloride was added carefully and stirring was continued for 0.5 hours. The precipitate was filtered off and washed with ethyl acetate. The product crystallized from the filtrate and was washed with water and a mixture of dichloromethane and methanol to give 3.13 g (79%) of the title compound.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with ethyl acetate
  3. customThe product crystallized from the filtrate
  4. washwas washed with water
  5. additiona mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-c0bd9be012c1474e922b0dcbfbce3092
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

Loading…