tert-Butyl methyl ether → HCID 178501315, compound

HRID 2052990Notes

Reaction equation

HRID 2052990 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)=[CH:10]2)[CH2:6]1)=[O:4].C(OC)(C)(C)C>C(OC(=O)C)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][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:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:20]=3)=[CH:10]2)[CH2:8]1)=[O:4]

Participants

4

Reactant 2

HCID 15413tert-Butyl methyl etherHCID 178501314HCID 178501314, compound

Product 1

HCID 178501315HCID 178501315, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The cis/trans-3-[4-amino-5-(3-benzyloxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methyl ester mixture is prepared as described in Example 47(a) of WO 97/28161. The cis-3-[4-amino-5-(3-benzyloxy-phenyl)pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutanecarboxylic acid methyl ester is isolated from the cis/trans mixture by chromatography on silicagel (t-butyl-methyl-ether:ethylacetate=1:1). Analytical HPLC: tR=10.59 min (Grad 1); ES-MS m/eo=429.

Sources & evidence

ORD record
ord-6244ccb97fea4d958b095f05a1d1f3ea
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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