Chlorotrimethylsilane → 10-hydroxymethyl-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 2393404Notes

Reaction equation

HRID 2393404 reaction equation
[CH3:1][C:2]1(CCCCC(OCC)=O)[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.CC1C2N3C=CN=C3[C:38](=[O:45])NC=2C2C=CC=CC1=2.[H-].[Na+].C[Si](Cl)(C)C.O1CCCOO1>CN(C)C=O>[OH:45][CH2:38][C:2]1([CH3:1])[C:14]2[N:13]3[CH:15]=[CH:16][N:17]=[C:12]3[C:11](=[O:18])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 24758Sodium hydrideHCID 18975437ethyl 5-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]-pyrazin-10-yl)valerateHCID 1897544610-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 19593658CID 19593658

Product 1

HCID 1897543310-hydroxymethyl-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The process is performed as in Example 50 for the preparation of ethyl 5-(10-methyl-4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-10-yl)-valerate but starting with 0.48 g of 10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 25 ml of dimethylformamide, 0.33 g of sodium hydride, 0.28 ml of trimethylsilyl chloride and 0.1 g of trioxane. 0.27 g of 10-hydroxymethyl-10-methyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is obtained in the form of a pale yellow solid melting above 260° C. (Analysis, % calculated C: 67.41, H: 4.90, N: 15.72, O: 11.97, % found C: 67.4, H: 4.9, N: 15.7).

Sources & evidence

ORD record
ord-73a30467a2c94e0d8efcf703f7c82795
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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