Tetramethyltin → HCID 178501316, compound

HRID 2053019Notes

Reaction equation

HRID 2053019 reaction equation
[CH3:1][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]2Br)[CH2:6]1)=[O:4].[CH3:34][Sn](C)(C)C>CN(C)C=O>[CH3:1][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[CH3:34])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 11661TetramethyltinHCID 178501312HCID 178501312, compound

Product 1

HCID 178501316HCID 178501316, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound is prepared in analogy to Example 104 starting from 6.6 g (12.6 mmol) cis-3-[4-amino-5-(3-benzyloxy-phenyl)-6-bromo-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutane-carboxylic acid methyl ester of Example 113, 0.364 g (0.315 mmol) tetrakistriphenyl palladium, and 4.39 ml (31.52 mmol) tin tetramethyl (Fluka, Buchs, Switzerland) in 20 ml dry N,N-dimethylformamide (T=100-110° C., sealed tube; reaction time=25 h). Analytical HPLC: tR=11.67 min (Grad 1); ES-MS: m/eo=443.2; NMR (DMSO-d6; not all signals reported): 8.07/s (1H), 7.25-7.5/several m's (6H), 7.03/“d” (1H); 6.95/s (1H); 6.90/“d” (1H); 5.5-6.0/b (NH2); 5.14/s (2H); 4.90/m (1H); 3.65/s (3H); 2.25/s (3H).

Sources & evidence

ORD record
ord-5d2789f5db9e44fe84d2503c433d30e9
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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