tert-Butanol → HCID 59468607, compound

HRID 1012174Notes

Reaction equation

[C:1]1([CH3:22])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[N:13]=[C:12]([C:14]3[S:18][C:17](C(O)=O)=[CH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[CH3:47][C:48]([OH:51])([CH3:50])[CH3:49]>>[C:48]([O:51][C:45](=[O:30])[NH:42][C:17]1[S:18][C:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([NH:7][C:3]3[CH:2]=[C:1]([CH3:22])[CH:6]=[CH:5][CH:4]=3)[N:13]=2)=[CH:15][CH:16]=1)([CH3:50])([CH3:49])[CH3:47]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 59468598HCID 59468598, compound

Product 1

HCID 59468607HCID 59468607, compoundYield 41.1%

Procedure

5-(2-m-Tolylamino-pyrimidin-4-yl)thiophene-2-carboxylic acid (200 mg, 0.643 mmol) was treated with Diphenylphosphorylazide (277 uL, 1.28 mmol) and triethylamine (180 uL, 1.28 mmol) in t-BuOH (4 mL) for 7 hours at 100° C. The reaction was cooled to room temperature, concentrated in vacuo and purified by SiO2 chromatography (0-50% B over 25 min.; Hexanes/EtOAc) to afford [5-(2-m-Tolylamino-pyrimidin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester (101.8 mg, 41.1%). 1H NMR (500 MHz, DMSO-d6) δ 1.49 (s, 9H), 2.32 (s, 3H), 6.57 (d, J=4 Hz, 1H), 6.75 (d, J=8 Hz, 1H), 7.13 (t, J=8 Hz, 1H), 7.14 (d, J=5 Hz, 1H), 7.47 (br m, 1H), 7.68 (d, J=4 Hz, 1H), 7.83 (br s, 1H), 8.32 (d, J=5 Hz, 1H), 9.42 (s, 1H), 10.8 (br s, 1H). MS: m/z 383 (M+H+).

Workup

concentrationconcentrated in vacuo
custompurified by SiO2 chromatography (0-50% B over 25 min.; Hexanes/EtOAc)

Sources & evidence

ORD record: ord-7acc4e1ef81143c8aeccdea86b2a74ed
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977481B2

Reaction notes

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