Formaldehyde → tert-Butyl 7-Methyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-carbamate

HRID 1411974Notes

Reaction equation

HRID 1411974 reaction equation
[N:1]1[C:2]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:3][N:4]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=12.C=O.[BH3-][C:21]#N.[Na+]>[Cl-].[Cl-].[Zn+2].C(OCC)C.CO>[CH3:21][N:7]1[CH2:8][CH2:9][N:4]2[N:3]=[C:2]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[N:1]=[C:5]2[CH2:6]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86684511tert-Butyl (5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)carbamate

Product 1

HCID 86684510tert-Butyl 7-Methyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-carbamateYield 94%

Reagents, catalysts & solvents 2

HCID 162251561ZINC;ethoxyethane;dichlorideCatalystHCID 887MethanolSolvent

Procedure

Following the procedure in Example 191i, and starting with 270d (500 mg, 2.1 mmol, 1.0 eq.), paraformaldehyde (630 mg, 21.0 mmol, 10.0 eq.), ZnCl2/diethyl ether (2.1 mL, 2.1 mmol, 1.0 M), NaBH3CN (390 mg, 6.3 mmol, 3.0 eq.), and methanol (20 mL) afforded 270e as a yellow solid (500 mg, 94%). MS-ESI: [M-tBu]+ 198.0.

Sources & evidence

ORD record
ord-d1d7a4b917ce4194abc471de40c391f4
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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