Aluminium lithium hydride → HCID 178435367, compound

HRID 2053026Notes

Reaction equation

HRID 2053026 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([N:9]2[C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]=3[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)=[C:10]2[CH2:33][CH3:34])[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:18][C:17]1[C:12]2[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)=[C:10]([CH2:33][CH3:34])[N:9]([C@@H:7]3[CH2:6][C@H:5]([CH2:3][OH:2])[CH2:8]3)[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178435369HCID 178435369, compound

Product 1

HCID 178435367HCID 178435367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In analogy to Example 105, 0.73 g (1.56 mmol) cis-3-[4-amino-5-(3-benzyloxy-phenyl)-6-ethyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methyl ester of Example 123 are reduced with 69 mg (1.73 mmol) lithium aluminiumhydride in THF. Reaction time: 18 h at 0-5° C. Analytical HPLC: tR=11.15 min (Grad 1); ES-MS: m/eo=429.1; NMR (DMSO-d6): 8.10/s (1H); 7.3-7.5/several m's (6H), 7.04/“d” (1H); 6.93/s (1H); 6.90/“d” (1H); 5.4-6.0/b (NH2); 5.15/s (2H); 4.75/m (1H); 4.63/“t” (OH); 3.60/t (2H); 3.03 q (2H); 2.61/q (2H); 2.14/q (2H); 2.24/m (1H); 1.07/t (3H).

Workup

  1. customReaction time
  2. custom18 h
  3. customat 0-5° C

Sources & evidence

ORD record
ord-20cee2fdc6a641919c01ee16bc500b4b
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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