Tetrabutylammonium Fluoride → 3-[4-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-6-hydroxymethyl-3H-thieno[3,2-d]pyrimidin-4-one

HRID 72241Notes

Reaction equation

HRID 72241 reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[S:16][C:15]2[C:14](=[O:17])[N:13]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:28][CH2:27][CH:26]([N:29]([CH3:31])[CH3:30])[CH2:25]4)=[CH:20][CH:19]=3)[CH:12]=[N:11][C:10]=2[CH:9]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:30][N:29]([CH3:31])[CH:26]1[CH2:27][CH2:28][N:24]([C:21]2[CH:20]=[CH:19][C:18]([N:13]3[C:14](=[O:17])[C:15]4[S:16][C:8]([CH2:7][OH:6])=[CH:9][C:10]=4[N:11]=[CH:12]3)=[CH:23][CH:22]=2)[CH2:25]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317318266-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[4-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-3H-thieno[3,2-d]pyrimidin-4-one

Product 1

HCID 689754473-[4-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-6-hydroxymethyl-3H-thieno[3,2-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-[4-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-3H-thieno[3,2-d]pyrimidin-4-one (1.4 g) and 1 M solution of Tetra-N-butylammoniumfluoride in THF (2.7 mL) in THF (20.0 mL) was stirred at room temperature for 3 h. The solvent was removed in vacuo and the crude product was purified by preparative HPLC. The product with the molecular weight of 370.47 (C19H22N4O2S) was obtained in this way; MS (ESI): 371 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by preparative HPLC
  3. customThe product with the molecular weight of 370.47 (C19H22N4O2S) was obtained in this way

Sources & evidence

ORD record
ord-c4f744aaedc04c0d8f76054d7b1cc498
Source dataset
uspto-grants-2014_09
Patent number
US08828991B2

Reaction notes

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