Dimethylacetamide → 2-Amino-4-cyano-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 237398

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13](Cl)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].C[C:18]([N:20](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13]([C:18]#[N:20])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

2-Amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1 equiv.), Zn(CN)2 (0.6 equiv.), Zn dust (0.12 equiv.), Pd2(dba)3 (0.02 mole eq.) and 1,1′-bis(diphenylphosphino)ferrocene (0.04 equiv.) were mixed in DMA and the mixture was stirred under argon at 120° C. for 24 hours. The resulting suspension was filtered through a short Celite column, the filtrate was diluted with brine and extracted with ethyl acetate. The organic layer was then washed with brine, water and dried over sodium sulphate. After evaporation of the solvent, the crude oil was purified by preparative TLC.

Workup

filtrationThe resulting suspension was filtered through a short Celite column
additionthe filtrate was diluted with brine
extractionextracted with ethyl acetate
washThe organic layer was then washed with brine, water
dry with materialdried over sodium sulphate
customAfter evaporation of the solvent
customthe crude oil was purified by preparative TLC

Sources & evidence

ORD record: ord-8ac7a9a78b8c4221be440008c345952c
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642594B2

Linked notes

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