Water → methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-5-ylcarbamate

HRID 2174295Notes

Reaction equation

HRID 2174295 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[N:8][C:7]([C:15]2[N:20]=[C:19]([NH2:21])[C:18]([NH2:22])=[C:17]([NH2:23])[N:16]=2)=[N:6]1.Cl[C:29]([O:31][CH3:32])=[O:30].O>N1C=CC=CC=1>[NH2:23][C:17]1[C:18]([NH:22][C:29](=[O:30])[O:31][CH3:32])=[C:19]([NH2:21])[N:20]=[C:15]([C:7]2[N:8]=[C:9]([C:10]3[S:11][CH:12]=[CH:13][N:14]=3)[N:5]([CH2:4][C:3]3[CH:24]=[CH:25][CH:26]=[CH:27][C:2]=3[F:1])[N:6]=2)[N:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformate2×HCID 690933152-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4,5,6-triamine

Product 1

HCID 69092853methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-5-ylcarbamateYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-4,5,6-triamine (I-57, 0.31 mmol) in pyridine (2.0 mL) at 0° C. was treated with methyl chloroformate (1 equiv). After 30 min, additional portions of methyl chloroformate (3 equiv) were added and the reaction was stirred for 3 h. The reaction mixture was poured into water and the resultant tan solid was collected by filtration to afford methyl 4,6-diamino-2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)pyrimidin-5-ylcarbamate (74% yield).

Workup

  1. filtrationthe resultant tan solid was collected by filtration

Sources & evidence

ORD record
ord-0dd92044d40144a98e0224956b540f0b
Source dataset
uspto-grants-2015_06
Patent number
US09061030B2

Reaction notes

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