Sodium triacetoxyborohydride → tert-butyl N-[4-[[[(6S)-4-oxo-3-(2-phenylethylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HRID 10957Notes

Reaction equation

[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:12][CH:11]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[C:39](OC(=O)NC(C1C=CC(CNC([C@H]2N3C(=O)C(N)=CN=C3CC2)=O)=CC=1)=N)(C)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8](=[NH:9])[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18]([C@H:20]2[N:24]3[C:25](=[O:37])[C:26]([NH:29][CH2:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:39]=4)=[CH:27][N:28]=[C:23]3[CH2:22][CH2:21]2)=[O:19])=[CH:14][CH:15]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 145857226tert-butyl N-[4-[[[(6S)-3-amino-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

HCID 145857234tert-butyl N-[4-[[[(6S)-3-(benzylamino)-4-oxo-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamate

Product 1

HCID 145857194tert-butyl N-[4-[[[(6S)-4-oxo-3-(2-phenylethylamino)-7,8-dihydro-6H-pyrrolo[1,2-a]pyrimidine-6-carbonyl]amino]methyl]benzenecarboximidoyl]carbamateYield 54%

Procedure

Following a procedure similar to that for the preparation of 1k, intermediate 1j (60 mg, 0.14 mmol), phenylacetyladehyde (67.3 mg, 0.56 mmol) and NaBH(OAc)3 (326.4 mg, 1.54 mmol) yielded 40 mg (54%) of intermediate 2a. MS (ESI) 531.1 (M+H+).

Sources & evidence

ORD record: ord-4dd495067f7e4572983b6e970c23d3a3
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094783B2

Reaction notes

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