Chlorotrimethylsilane → HCID 178511176, compound

HRID 1447148Notes

Reaction equation

HRID 1447148 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[Si](C)(C)C.[C:30]([CH2:32][C:33](Cl)=[O:34])#[N:31]>ClCCl>[C:30]([CH2:32][C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:6][CH:7]=1)=[O:34])#[N:31]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 110515942-Cyanoacetyl chlorideHCID 178507442HCID 178507442, compound

Product 1

HCID 178511176HCID 178511176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the method for the preparation of the side chain acid in Example 1, 9.2 g (40 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 16.8 ml (120 mmol) of triethylamine, 16 ml (126 mmol) of chlorotrimethylsilane, 400 ml of dichloromethane, and 5.0 (45 mmol) of cyanoacetyl chloride [Org. Syn. Col. Vol. V, p. 171] gives 12.3 g of 2-[4-(cyanoacetylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid as the monohydrate; mp>280°.

Sources & evidence

ORD record
ord-de50ba39e1684a2b90a1f06bcb6fbf51
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

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