Water → 7-(Diisopropylamino)-2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidine-5-carbaldehyde

HRID 32609Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13](SC)[C:14]=3[N:15]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=[CH:3]1.[Li+].[CH3:25][CH:26]([N-:28][CH:29]([CH3:31])[CH3:30])[CH3:27].CN([CH:35]=[O:36])C.O>C1COCC1>[CH:26]([N:28]([CH:29]([CH3:31])[CH3:30])[C:13]1[C:14]2[N:15]=[C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][C:5]=3[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[S:8][C:9]=2[N:10]=[C:11]([CH:35]=[O:36])[N:12]=1)([CH3:27])[CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-(1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 42) (0.1 g) in THF (4 mL) was added to a solution of LDA (2.2 eq) in THF (6 mL) at −78° C., under an inert atmosphere. The reaction mixture was stirred at −78° C. for 1 hours then DMF (0.4 mL) was added. The reaction mixture was stirred at −78° C. for a further 1 hours then poured into water (10 mL) and extracted with EtOAc (3×10 mL), washed with brine (10 mL), dried and the solvent evaporated in vacuo to give a brown oil. Purification by flash chromatography on silica, eluting with EtOAc:hexane (1:9) gave the title compound as a yellow oil (14 mg, 11%);

Workup

stirringThe reaction mixture was stirred at −78° C. for a further 1 hours
extractionextracted with EtOAc (3×10 mL)
washwashed with brine (10 mL)
customdried
customthe solvent evaporated in vacuo
customto give a brown oil
customPurification by flash chromatography on silica
washeluting with EtOAc:hexane (1:9)

Sources & evidence

ORD record: ord-d1044b0e3619404bbf9a5a3b8ca767c4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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